Nitrogen-containing compounds and harmful organism control agents

ABSTRACT

The present invention provides a nitrogen-containing compound represented by formula (I 1 ) (in formula (I 1 ), R 0  represents a nitro group or the like, Z represents an optionally substituted aryl group or the like, R 3  represents a hydrogen atom or the like, Y represents a nitro group or the like, n represents an integer of 0 to 3, D represents an optionally substituted 5-membered to 8-membered hydrocarbon ring group or heterocyclic group having or not having a substituent other than substituent X, X represents a group represented by formula (II-1) (in formula (II-1), R 1  and R 2  respectively and independently represent a hydrogen atom or the like), A represents a carbon atom or the like, n1 represents an integer of 0 to 2) or a salt thereof, and an insecticide, miticide, sanitary insect pest control agent, or harmful organism control agent including as an active ingredient thereof the nitrogen-containing compound or the salt thereof.

TECHNICAL FIELD

The present invention relates to a new nitrogen-containing compound orsalt thereof, and an insecticide, miticide, sanitary insect pest controlagent or a harmful organism control agent containing at least one ormore types of the compounds.

Priority is claimed on Japanese Patent Application No. 2009-028534,filed Feb. 10, 2009, the content of which is incorporated herein byreference.

BACKGROUND ART

Until now, various insecticides, miticides or the like have been used inagriculture, horticulture, animal farming, building, houses, residentialbuildings or the like. However, since the efficacy of the conventionalproducts has been inadequate, their use has been limited due to problemswith drug resistance, or they have caused damage or contamination toplants or demonstrated potent toxicity against humans, livestock orfish, and there have been more than a few cases in which theseconventional pest control agents were hardly considered to besatisfactory control agents. Thus, there has been a desire for thedevelopment of a chemical having few of these disadvantages that canalso be used safely.

Patent document 1 relating to the present invention describes thefollowing compound having a backbone that resembles that of the compoundaccording to the present invention. Patent document 1 does not describethe nitrogen-containing compound of the present invention. In theformula, A1, A2, A3 and A4 respectively and independently represent acarbon atom or nitrogen atom, G1 represents benzene ring, a 6-memberednitrogen-containing aromatic compound, G2 represents a structurerepresented by formula (G2-1), (G2-2) or the like. However, the compounddescribed in Patent document 1 was not considered to always demonstrateadequate control effects.

PRIOR ART LITERATURE Patent Document

-   Patent document 1: WO2009/005015

DISCLOSURE OF INVENTION Problems to be Solved by the Invention

An object of the present invention is to provide a novelnitrogen-containing compound or salt thereof, which can beadvantageously synthesized industrially and can function as an activeingredient of a harmful organism control agent that has reliable effectsand can be used safely; and an insecticide, miticide, sanitary insectpest control agent or harmful organism control agent that contains as anactive ingredient thereof at least one type of these compounds.

Means for Solving the Problems

As a result of conducting extensive studies to achieve the aboveobjective, the inventors of the present invention discovered that anitrogen-containing compound represented by formula (I) or a saltthereof can be advantageously synthesized industrially and can functionas an active ingredient of a harmful organism control agent that hasreliable effects and can be used safely. The present invention wasachieved on the basis of this perception.

Namely, the present invention is a nitrogen-containing compoundrepresented by formula (I) or a salt thereof. In addition, the presentinvention is an insecticide, a miticide, a sanitary insect pest controlagent or a harmful organism control agent including as an activeingredient thereof at least one of the nitrogen-containing compoundsrepresented by formula (I) or the salts thereof.

In formula (I), R⁰ represents a nitro group, hydroxyl group, mercaptogroup, a halogen group, an optionally substituted amino group, or anorganic group, preferably represents an organic group, and morepreferably represents a C1 to C12 haloalkyl group.

In formula (I), Z represents an optionally substituted aryl group, anoptionally substituted heterocyclic group, an optionally substitutedalkyl group, an optionally substituted alkenyl group or an optionallysubstituted alkynyl group, preferably represents an optionallysubstituted phenyl group or an optionally substituted 5-membered or6-membered heterocyclic group including at least one heteroatom selectedfrom the group consisting of a nitrogen atom, oxygen atom and sulfuratom.

R³ represents a hydrogen atom, an optionally substituted aryl group, anoptionally substituted heterocyclic group, an optionally substitutedalkyl group, an optionally substituted alkenyl group, an optionallysubstituted alkynyl group or an acyl group.

In formula (I), Q represents a group represented by formula (I′).

In formula (I′), Y represents a nitro group, hydroxyl group, mercaptogroup, a halogen atom, an optionally substituted amino group or anorganic group, preferably presents a halogen atom, a C1 to C6 alkylgroup, a C1 to C6 alkoxy group, a C1 to C6 haloalkyl group or a C1 to C6haloalkoxy group, and more preferably represents a halogen atom or a C1to c6 haloalkyl group.

n represents an integer of 0 to 3, and preferably represents 0. Inaddition, a plurality of Y may be identical to or different from eachother when n is 2 or more. In addition, two Y may bond together to froma 4-membered to 6-membered ring when the two Y are mutually adjacent.

In formula (I′), D represents a 5-membered to 8-membered hydrocarbonring group or heterocyclic group not having or having a substituentother than substituent X.

In formula (I′), X represents a group represented by the followingformula (II-1) or (II-2), and preferably represents a group representedby formula (II-1).

In formula (II-1), R¹ and R² respectively and independently represent ahydrogen atom, nitro group, hydroxyl group, mercapto group, anoptionally substituted amino group or an organic group. R¹ and R² maybond together to form a 3-membered to 8-membered ring.

R¹ or R² may bond to A to form a 5-membered or 8-membered ring.

In formula (II-1), R¹ preferably represents a group represented byformula (III).

In formula (III), R¹³⁰ represents a hydrogen atom, hydroxyl group,mercapto group, a halogen atom, an optionally substituted amino group ororganic group, and more preferably represents a hydrogen atom, anoptionally substituted amino group or an organic group. W represents anoxygen atom or sulfur atom, and more preferably represents an oxygenatom.

In formula (II-2), W represents an oxygen atom or sulfur atom. R¹¹represents a hydrogen atom, oxygen atom, mercapto group, an optionallysubstituted amino group or an organic group.

In formula (I′), A represents a carbon atom or nitrogen atom. In thecase where A is a carbon atom and does not have a substituentrepresented by Y on the carbon atom, a hydrogen atom bonds thereto or Aforms a ring by bonding to R¹ or R².

In formula (I′), n1 represents an integer of 0 to 2. Two X may beidentical to or different from each other when n1 is 2.

Q represented by formula (I′) is preferably represented by formula (IV).

In addition, in formula (IV), A, Y, n, X and n1 have the same meaning asdescribed above.

Effects of the Invention

According to the present invention, a novel nitrogen-containing compoundor salt thereof, which can be advantageously synthesized industriallyand can function as an active ingredient of a pest control agent thathas reliable effects and can be used safely is provided.

In addition, according to the present invention, an insecticide,miticide, sanitary insect pest control agent or a harmful organismcontrol agent, which contains as an active ingredient among thesecompounds at least one type of the compound, are provided.

BEST MODE FOR CARRYING OUT THE INVENTION

The present invention will be described in detail.

1) Nitrogen-containing Compound or Salt Thereof.

The present invention is a nitrogen-containing compound represented byformula (I) (hereafter, nitrogen-containing compound of the presentinvention) or a salt thereof.

In formula (I), R⁰ represents a nitro group, hydroxyl group, mercaptogroup, a halogen atom, an optionally substituted amino group or anorganic group.

Examples of the halogen atom include a fluorine atom, chlorine atom,bromine atom or the like.

Examples of the optionally substituted amino group include an aminogroup; mono-C1 to C6 alkylamino groups such as a methylamino group,ethylamino group or i-propylamino group; di-C1 to C6 alkylamino groupssuch as a dimethylamino group or diethylamino group; acylamino groupssuch as an acetylamino group or benzoylamino group; an optionallysubstituted arylamino groups such as a phenylamino group or4-methylphenylamino group; and the like.

The aforementioned organic group refers to an atom group that contains acarbon atom. Examples of the organic group include a cyano group; a C1to C6 alkyl group such as a methyl group, ethyl group, n-propyl group,i-propyl group, n-butyl group, i-butyl group, s-butyl group, t-butylgroup, n-pentyl group or n-hexyl group; a C2 to C6 alkenyl group such asa vinyl group, propenyl group, i-propenyl group, 2-butenyl group,3-butenyl group, 1-methyl-2-propenyl group, 2-methyl-2-propenyl group,1-pentenyl group, 2-pentenyl group, 3-pentenyl group, 4-pentenyl group,1-methyl-2-butenyl group, 2-methyl-2-butenyl group, 1-hexenyl group,2-hexenyl group, 3-hexenyl group, 4-hexenyl group or 5-hexenyl group; aC2 to C6 alkynyl group such as an ethynyl group, 1-propynyl group,2-propynyl group, 1-butynyl group, 2-butynyl group, propargyl group,3-butynyl group, 1-methyl-2-propynyl group, 2-methyl-3-butynyl group,1-pentynyl group, 2-pentynyl group, 3-pentynyl group, 4-pentynyl group,1-methyl-2-butynyl group, 2-methyl-3-pentynyl group, 1-hexynyl group or1,1-dimethyl-2-butynyl group; a C1 to C12 haloalkyl group such as achloromethyl group, dichloromethyl group, chloroethyl group,1,2-dichloro-n-propyl group, 1-fluoro-n-butyl group, perfluoro-n-pentylgroup, bromomethyl group, difluoromethyl group, trichloromethyl group,2,2,2-trifluoroethyl group, trifluoromethyl group or pentafluoroethylgroup; a C3 to C8 cycloalkyl group such as a cyclopropyl group,cyclobutyl group, cyclopentyl group, cyclohexyl group or cycloheptylgroup; a C3 to C8 halocycloalkyl group such as a 2-chlorocyclopropylgroup, 2,2-dichlorocyclopropyl group, 3-chlorocyclopentyl group or4-bromocyclohexyl group;

A C1 to C6 alkoxy group such as a methoxy group, ethoxy group, n-propoxygroup, i-propoxy group, n-butoxy group, t-butoxy group, i-butoxy group,s-butoxy group or n-hexyloxy group; a C1 to C6 haloalkoxy groups such asa 2-chloro-n-propoxy group, 2,3-dichlorobutoxy group, trichloromethoxygroup or trifluoromethoxy group; a C1 to C6 alkylsulfonyloxy groups suchas a methylsulfonyloxy group, ethylsulfonyloxy group ori-propylsulfonyloxy group; arylsulfonyloxy groups such as aphenylsulfonyloxy group or 4-methylphenylsulfonyloxy group; a C1 to C6alkylthio group such as a methylthio group, ethylthio group,n-propylthio group, i-propylthio group, n-butylthio group, i-butylthiogroup, s-butylthio group or t-butylthio group; a C1 to C6 alkylsulfinylgroup such as a methylsulfinyl group, ethylsulfinyl group,n-propylsulfinyl group or t-butylsulfinyl group; a C1 to C6alkylsulfonyl groups such as a methylsulfonyl group, ethylsulfonylgroup, n-propylsulfonyl group or t-butylsulfonyl group; a C1 to C6haloalkylthio group such as a chloromethylthio group,trichloromethylthio group or trifluoromethylthio group; a C1 to C6haloalkylsulfinyl group such as a chloromethylsulfinyl group,trichloromethylsulfinyl group or trifluoromethylsulfinyl group; a C1 toC6 haloalkylsulfonyl group such as a chloromethylsulfonyl group,trichloromethylsulfonyl group or trifluoromethylsulfonyl group; arylthiogroups such as a phenylthio group, 4-methylphenylthio group or2,4-dichlorophenylthio group; arylsulfinyl groups such as aphenylsulfinyl group, 4-methylphenylsulfinyl group or2,4-dichlorophenylsulfinyl group; arylsulfonyl groups such as aphenylsulfonyl group, 4-methylphenylsulfonyl group or2,4-dichlorophenylsulfonyl group; groups represented by —N═C(R³¹)OR⁴¹;groups represented by —COR³¹; groups represented by —C(═S)R³¹; groupsrepresented by —Si(R⁵¹)(R⁶¹)(R⁷¹; aryl groups such as a phenyl group,4-methylphenyl group, 2-fluorophenyl group, 2,4-dichlorophenyl group,2,4,6-trimethylphenyl group or 2-naphthyl group; and heterocyclicgroups.

The heterocyclic group is preferably a 3-membered to 8-membered ring andmore preferably a 5-membered or 6-membered ring. Specific examples ofthe heterocyclic group include unsaturated heterocyclic 5-membered ringgroups such as a furan-2-yl group, furan-3-yl group, thiophen-2-ylgroup, thiophen-3-yl group, pyrrol-2-yl group, pyrrol-3-yl group,oxazol-2-yl group, oxazol-4-yl group, oxazol-5-yl group, thiazol-2-ylgroup, thiazol-4-yl group, thiazol-5-yl group, isoxazol-3-yl group,isoxazol-4-yl group, isoxazol-5-yl group, isothiazol-3-yl group,isothiazol-4-yl group, isothiazol-5-yl group, imidazol-2-yl group,imidazol-4-yl group, imidazol-5-yl group, pyrazol-3-yl group,pyrazol-4-yl group, pyrazol-5-yl group or 1,3,4-oxadiazol-2-yl group,1,3,4-thiadiazol-2-yl group, 1,2,3-triazol-4-yl group,1,2,4-triazol-3-yl group or 1,2,4-triazol-5-yl group, unsaturatedheterocyclic 6-membered ring group such as a pyridin-2-yl group,pyridin-3-yl group, pyridin-4-yl group, 5-chloro-3-pyridyl group,3-trifluoromethyl-2-pyridyl group, pyridazin-3-yl group, pyridazin-4-ylgroup, pyrazin-2-yl group, pyrimidin-5-yl group, 1,3,5-triazin-2-ylgroup or 1,2,4-triazin-3-yl group, and saturated or partiallyunsaturated heterocyclic groups such as a tetrahydrofuran-2-yl group,tetrahydropyran-4-yl group, piperidin-3-yl group, pyrrolidin-2-yl group,morpholino group, piperidino group, piperazino group, N-methylpiperazinogroup, aziridino group, azetidino group, pyrrolidino group, morpholinogroup or oxazolin-2-yl group.

Among them, the unsaturated heterocyclic groups are preferable, and theunsaturated nitrogen-containing heterocyclic groups are more preferable.Specific examples thereof include a pyrrol-2-yl group, pyrrol-3-ylgroup, oxazol-2-yl group, oxazol-4-yl group, oxazol-5-yl group,thiazol-2-yl group, thiazol-4-yl group, thiazol-5-yl group,isoxazol-3-yl group, isoxazol-4-yl group, isoxazol-5-yl group,isothiazol-3-yl group, isothiazol-4-yl group, isothiazol-5-yl group,imidazol-2-yl group, imidazol-4-yl group, imidazol-5-yl group,pyrazol-3-yl group, pyrazol-4-yl group, pyrazol-5-yl group,1,3,4-oxadiazol-2-yl group, 1,3,4-thiadiazol-2-yl group,1,2,3-triazol-4-yl group, 1,2,4-triazol-3-yl group, 1,2,4-triazol-5-ylgroup, pyridin-2-yl group, pyridin-3-yl group, pyridin-4-yl group,5-chloro-3-pyridyl group, 3-trifluoromethyl-2-pyridyl group,pyridazin-3-yl group, pyridazin-4-yl group, pyrazin-2-yl group,pyrimidin-5-yl group, 1,3,5-triazin-2-yl group, 1,2,4-triazin-3-ylgroup, piperidin-3-yl group, pyrrolidin-2-yl group, morpholino group,piperidino group, piperazino group, N-methylpiperazino group, aziridinogroup, azetidino group, pyrrolidino group, morpholino group andoxazolin-2-yl group.

The aforementioned organic group may have a substituent at an arbitrarylocation within a chemically allowable range. The following listsexamples of groups capable of serving as such substituents:

(1) halogen atoms such as a fluorine atom, chlorine atom, bromine atomor iodine atom;

(2) alkyl groups such as a methyl group, ethyl group, n-propyl group,i-propyl group, n-butyl group, s-butyl group, i-butyl group, s-butylgroup, t-butyl group, n-pentyl group or n-hexyl group;

(3) cycloalkyl groups such as a cyclopropyl group, cyclobutyl group,cyclopentyl group, cyclohexyl group or cycloheptyl group;

(4) alkoxy groups such as a methoxy group, ethoxy group, n-propoxygroup, isopropoxy group, n-butoxy group, i-butoxy group, s-butoxy groupor t-butoxy group;

(5) alkenyl groups such as a vinyl group, 1-propenyl group, 2-propenylgroup, 1-butenyl group, 2-butenyl group, 3-butenyl group,1-methyl-2-propenyl group, 2-methyl-2-propenyl group, 1-pentenyl group,2-pentenyl group, 3-pentenyl group, 4-pentenyl group, 1-methyl-2-butenylgroup, 2-methyl-2-butenyl group, 1-hexenyl group, 2-hexenyl group,3-hexenyl group, 4-hexenyl group or 5-hexenyl group;

(6) cycloalkenyl groups such as a 2-cyclopropenyl group, 2-cyclopentenylgroup, 3-cyclohexenyl group or 4-cyclooctenyl group;

(7) alkenyloxy groups such as a vinyloxy group, allyloxy group,1-propenyloxy group or 2-butenyloxy group;

(8) alkynyl groups such as an ethynyl group, 1-propynyl group,2-propynyl group, 1-butynyl group, 2-butynyl group, 3-butynyl group,1-methyl-2-propynyl group, 2-methyl-3-butyryl group, 1-pentynyl group,2-pentynyl group, 3-pentynyl group, 4-pentynyl group, 1-methyl-2-butynylgroup, 2-methyl-3-pentynyl group, 1-hexynyl group or1,1-dimethyl-2-butynyl group;

(9) alkynyloxy groups such as an ethynyloxy group or propargyloxy group;

(10) aryl groups such as a phenyl group, 1-napthyl group or 2-naphthylgroup;

(11) aryloxy groups such as a phenoxy group or 1-naphthoxy group;

(12) aralkyl groups such as a benzyl group or phenethyl group;

(13) aralkyloxy groups such as a benzyloxy group or phenethyloxy group;

(14) acyl groups such as a formyl group, acetyl group, propionyl group,benzoyl group, cyclohexylcarbonyl group or phthaloyl group;

(15) alkoxycarbonyl groups such as a methoxycarbonyl group,ethoxycarbonyl group, n-propoxycarbonyl group, isopropoxycarbonyl group,n-butoxycarbonyl group or t-butoxycarbonyl group;

(16) carboxyl groups;

(17) hydroxyl groups;

(18) haloalkyl groups such as a chloromethyl group, chloroethyl group,1,2-dichloro-n-propyl group, 1-fluoro-n-butyl group orperfluoro-n-pentyl group;

(19) haloalkoxy groups such as 2-chloro-n-propoxy group, or2,3-dichlorobutoxy group, trifluoromethoxy group;

(20) haloalkenyl groups such as a 2-chloro-1-propenyl group or2-fluoro-1-butenyl group;

(21) haloalkynyl groups such as a 4,4-dichloro-1-butynyl group,4-fluoro-1-pentynyl group or 5-bromo-2-pentynyl group;

(22) haloalkenyloxy groups such as a 2-chloro-1-propenyloxy group or3-bromo-2-butenyloxy group;

(23) haloalkynyl groups such as a 3-chloro-propargyl group or3-iodo-propargyl group;

(24) haloalkynyloxy groups such as a 3-chloro-propargyloxy group or3-iodo-propargyloxy group;

(25) haloaryl groups such as a 4-chlorophenyl group, 4-fluorophenylgroup or 2,4-dichlorophenyl group;

(26) haloaryloxy groups such as a 4-fluorophenoxy group or4-chloro-1-naphthoxy group;

(27) halogen-substituted acyl groups such as a chloroacetyl group,trifluoroacetyl group, trichloroacetyl group or 4-chlorobenzoyl group;

(28) alkoxyalkyl groups such as a methoxymethyl group, ethoxymethylgroup, 1-ethoxyethyl group or 2-ethoxyethyl group;

(29) alkoxyalkoxy groups such as a methoxymethoxy group, ethoxymethoxygroup, 1-ethoxyethoxy group or 2-ethoxyethoxy group;

(30) cyano groups;

(31) isocyano groups;

(32) nitro groups;

(33) isocyanato groups;

(34) cyanato groups;

(35) amino groups;

(36) alkylamino groups such as a methylamino group, dimethylamino groupor diethylamino group;

(37) acylamino groups such as an anilino group, naphthylamino group oranthranylamino group;

(38) aralkylamino groups such as a benzylamino group or phenethylaminogroup;

(39) alkylsulfonylamino groups such as a methylsulfonylamino group,ethylsulfonylamino group, n-propylsulfonylamino group,isopropylsulfonylamino group or n-butylsulfonylamino group;

(40) arylsulfonylamino groups such as a phenylsulfonylamino group;

(41) heteroarylsulfonylamino groups such as a piperazinylsulfonylaminogroup;

(42) acylamino groups such as a formylamino group, acetylamino group,propanoylamino group, butyrylamino group, isopropylcarbonylamino groupor benzoylamino group;

(43) alkoxycarbonylamino groups such as a methoxycarbonylamino group orethoxycarbonylamino group;

(44) haloalkylsulfonylamino groups such as a fluoromethylsulfonylaminogroup, chloromethylsulfonylamino group, bromomethylsulfonylamino group,difluoromethylsulfonylamino group, dichloromethylsulfonylamino group,1,1-difluoroethylsulfonylamino group, trifluoromethylsulfonylaminogroup, 2,2,2-trifluoroethylsulfonylamino group orpentafluorosulfonylamino group;

(45) bis(alkylsulfonyl)amino groups such as a bis(methylsulfonyl)aminogroup, bis(ethylsulfonyl)amino group,(ethylsulfonyl)(methylsulfonyl)amino group, bis(n-propylsulfonyl)aminogroup, bis(isopropylsulfonyl)amino group, bis(n-butylsulfonyl)aminogroup or bis(t-butylsulfonyl)amino group;

(46) bis(haloalkylsulfonyl)amino groups such as abis(fluoromethylsulfonyl)amino group, bis(chloromethylsulfonyl)aminogroup, bis(bromomethylsulfonyl)amino group,bis(dichloromethylsulfonyl)amino group,bis(1,1-difluoroethylsulfonyl)amino group,bis(trifluoromethylsulfonyl)amino group, bis(2,2,2-trifluoroethyl)aminogroup or bis(pentafluoroethylsulfonyl)amino group;

(47) optionally substituted hydrazino groups such as a hydrazino group,N′-phenylhydrazino group, N′-methoxycarbonylhydrazino group,N′-acetylhydrazino group or N′-methylhydrazino group;

(48) optionally substituted aminocarbonyl groups such as anaminocarbonyl group, dimethylaminocarbonyl group, phenylaminocarbonylgroup or N-phenyl-N-methylcarbonyl group;

(49) optionally substituted hydrazinocarbonyl groups such as ahydrazinocarbonyl group, N′-methylhydrazinocarbonyl group orN′-phenylhydrazinocarbonyl group;

(50) optionally substituted iminoalkyl groups such as anN-methyliminomethyl group, 1-N-phenyliminoethyl group,N-hydroxyiminomethyl group or N-methoxyiminomethyl group;

(51) thiol groups;

(52) isothiocyanato groups;

(53) thiocyanato groups;

(54) alkylthio groups such as a methylthio group, ethylthio group,n-propylthio group, isopropylthio group, n-butylthio group, isobutylthiogroup, s-butylthio group or t-butylthio group;

(55) alkenylthio groups such as a vinylthio group or allylthio group;

(56) alkynylthio groups such as an ethynylthio group or propargylthiogroup;

(57) arylthio groups such as a phenylthio group or naphthylthio group;

(58) heteroarylthio groups such as a 2-piperidylthio group or3-pyridazylthio group;

(59) aralkylthio groups such as a benzylthio group or phenethylthiogroup;

(60) heteroarylalkylthio groups such as a 2-pyridylmethylthio group or2-furylmethylthio group;

(61) alkylthiocarbonyl groups such as a methylthiocarbonyl group,ethylthiocarbonyl group, n-propylthiocarbonyl group,isopropylthiocarbonyl group, n-butylthiocarbonyl group,isobutylthiocarbonyl group, s-butylthiocarbonyl group ort-butylthiocarbonyl group;

(62) alkylthioalkyl groups such as a methylthiomethyl group or1-methylthioethyl group;

(63) arylthioalkyl groups such as a phenylthiomethyl group or1-phenylthioethyl group;

(64) alkylthioalkoxy groups such as a methylthiomethoxy group or1-methylthioethoxy group;

(65) arylthioalkoxy groups such as a phenylthiomethoxy group or1-phenylthioethoxy group;

(66) allylsulfinyl groups such as a methylsulfinyl group, ethylsulfinylgroup or t-butylsulfinyl group;

(67) alkenylsulfinyl groups such as an allylsulfinyl group;

(68) alkynylsulfinyl groups such as a propargylsulfinyl group;

(69) arylsulfinyl groups such as a phenylsulfinyl group;

(70) heteroarylsulfinyl groups such as a 2-pyridylsulfinyl group or3-pyridylsulfinyl group;

(71) aralkylsulfinyl groups such as a benzylsulfinyl group orphenethylsulfinyl group;

(72) heteroarylalkylsulfinyl groups such as a 2-pyridylmethylsulfinylgroup or 3-pyridylmethylsulfinyl group;

(73) alkylsulfonyl groups such as a methylsulfonyl group, ethylsulfonylgroup or t-butylsulfonyl group;

(74) alkenylsulfonyl groups such as an allylsulfonyl group;

(75) alkynylsulfonyl groups such as a propargylsulfonyl group;

(76) arylsulfonyl groups such as a phenylsulfonyl group;

(77) heteroarylsulfonyl groups such as a 2-pyridylsulfonyl group or3-pyridylsulfonyl group;

(78) aralkylsulfonyl groups such as a benzylsulfonyl group orphenethylsulfonyl group;

(79) heteroarylalkylsulfonyl groups such as a 2-pyridylmethylsulfonylgroup or 3-pyridylmethylsulfonyl group;

(80) unsaturated heterocyclic 5-membered ring groups such as afuran-2-yl group, furan-3-yl group, thiophen-2-yl group, thiophen-3-ylgroup, pyrrol-2-yl group, pyrrol-3-yl group, oxazol-2-yl group,oxazol-4-yl group, oxazol-5-yl group, thiazol-2-yl group, thiazol-4-ylgroup, thiazol-5-yl group, isoxazol-3-yl group, isoxazol-4-yl group,isoxazol-5-yl group, isothiazol-3-yl group, isothiazol-4-yl group,isothiazol-5-yl group, imidazol-2-yl group, imidazol-4-yl group,imidazol-5-yl group, pyrazol-3-yl group, pyrazol-4-yl group,pyrazol-5-yl group, 1,3,4-oxadiazol-2-yl group, 1,3,4-thiadiazol-2-ylgroup, 1,2,3-triazol-4-yl group, 1,2,4-triazol-3-yl group or1,2,4-triazol-5-yl group;

(81) unsaturated heterocyclic 6-membered ring groups such as apyridin-2-yl group, pyridin-3-yl group, pyridin-4-yl group,5-chloro-3-pyridyl group, 3-trifluoromethyl-2-pyridyl group,pyridazin-3-yl group, pyridazin-4-yl group, pyrazin-2-yl group,pyrimidin-5-yl group, 1,3,5-triazin-2-yl group or 1,2,4-triazin-3-ylgroup;

(82) saturated or partially unsaturated heterocyclic groups such as atetrahydrofuran-2-yl group, tetrahydropyran-4-yl group, piperidin-3-ylgroup, pyrrolidin-2-yl group, morpholino group, piperidino group,N-methylpiperazino group or oxazolin-2-yl group;

(83) heterocyclooxy groups such as a 2-pyridyloxy group or3-isoxazolyloxy group;

(84) heteroarylalkyl groups such as a 2-pyridylmethyl group or3-pyridylmethyl group; and,

(85) heteroarylalkoxy groups such as a 2-pyridylmethoxy group or3-pyridylmethoxy group.

These substituents exemplified in (1) to (85) above can also havesubstituents exemplified in (1) to (85).

Specific examples of the heterocyclic groups having substituents includea 3-trifluoromethylpyridin-2-yl group, 4-trifluoromethoxy-2-pyridylgroup, 3-methyl-1-pyrazolyl group, 4-trifluoromethyl-1-imidazolyl group,3,4,-difluoropyrrolidino group and 2-trifluoromethyl-4-pyrimidyl group.

R³¹ and R⁴¹ respectively and independently represent a hydrogen atom,hydroxyl group, an optionally substituted hydrazine group, an optionallysubstituted amino group, or an organic group.

Among these, R³¹ is preferably a hydrogen atom; a C1 to C12 alkyl groupsuch as a methyl group or ethyl group; a C1 to C12 haloalkyl group suchas a trifluoromethyl group or pentafluoroethyl group; a C3 to C12cycloalkyl group such as a cyclopropyl group, cyclopentyl group orcyclohexyl group; a C2 to C12 alkenyl group such as a vinyl group orallyl group; a C2 to C12 haloalkenyl group such as a 3-chloroallylgroup; a C2 to C12 alkynyl group such as a propargyl group or 3-butynylgroup; a C2 to C12 haloalkynyl group such as a 2-chloroethynyl group,2-bromoethynyl group or 3,3,3-trifluoro-1-propynyl group; a C1 to C12alkylthio group such as a methylthio group or ethylthio group; hydroxylgroup; a C1 to C12 alkoxy group such as a methoxy group or ethoxy group;amino group; mono-C1 to C6 alkylamino group such as a methylamino groupor ethylamino group; di-C1 to C6 alkylamino group such as adimethylamino group or diethylamino group; acylamino group such as anacetylamino group or benzoylamino group; an optionally substitutedarylamino group such as a phenylamino group or 4-methylphenylaminogroup; an optionally substituted aryl group such as a phenyl group,4-methylphenyl group, 2-chlorophenyl group or 2,4-difluorophenyl group;an optionally substituted heterocyclic group; or an optionallysubstituted hydrazdino group such as an N′-methylhydrazino group,N′-phenylhydrazino group or N,N′-dimethylhydrazino group.

R⁴¹ is preferably a hydrogen atom; a C1 to C12 alkyl group such as amethyl group or ethyl group; a C1 to C12 haloalkyl group such as atrifluoromethyl group or pentafluoroethyl group; a C3 to C12 cycloalkylgroup such as a cyclopropyl group, cyclopentyl group or cyclohexylgroup; a C2 to C12 alkenyl group such as a vinyl group or allyl group; aC2 to C12 haloalkenyl group such as a 3-chloroallyl group; a C2 to C12alkynyl group such as a propargyl group or 3-butynyl group; a C2 to C12haloalkynyl group such as a 2-chloroethynyl group, 2-bromoethynyl groupor 3,3,3-trifluoro-1-propynyl group; amino group; di-C1 to C6 alkylaminogroup such as a dimethylamino group or diethylamino group; an optionallysubstituted arylamino group such as a phenylamino group or4-methylphenylamino group; an optionally substituted aryl group such asa phenyl group, 4-methylphenyl group, 2-chlorophenyl group or2,4-difluorophenyl group; or an optionally substituted heterocyclicgroup.

Specific examples of the group represented by the aforementioned formula—N═C(R³¹)OR⁴¹ include —N═C(H)OCH₃, —N═C(CH₃)OCH₃, —N═C(CH₃)OPh,—N═C(CF₃)OC₂H₅, —N═C(CH₃)OCH₂CH═CH₂ and —N═C(CH₃)OcPr. Here, cPrrepresents a cyclopropyl group, Ph represents a phenyl group (and tomean the same hereinafter).

Specific examples of the group represented by the aforementioned formula—COR³¹ include —C(═O)NH(CH₃), —C(═O)N(CH₃)₂, —C(═O)N(CH₃)Ph,—C(═O)N(CF₃)C₂H₅, —C(═O)N(CH₃)CH₂CH═CH₂, —C(═O)N(CH₃)(cPen), —CHO,—CO₂CH₃, —CO₂C₂H₅, —CO₂Ph, —CO₂CH₂CH═CH₂ and —CO₂CF₃. The aforementionedcPen represents a cyclopentyl group (and to mean the same hereinafter).

Specific examples of the group represented by the aforementioned formula—C(═S)R³¹ include —C(═S)NH(C₃H₇), —C(═S)N(C₂H₅)₂, —C(═S)N(CH₃)Ph,—C(═S)N(CF₃)(n-C₄H₉), —C(═S)N(CH₃)CH₂CH═CH₂, —C(═S)N(CH₃)(cHex),—C(═S)Ph and —C(═S)(n-C₄H₉). The aforementioned cHex represents acyclohexyl group (and to mean the same hereinafter).

R⁵¹, R⁶¹ and R⁷¹ respectively and independently represent a hydrogenatom; a C1 to C12 alkyl group such as a methyl group, ethyl group,n-propyl group, i-propyl group, n-butyl group or t-butyl group; anoptionally substituted aryl group such as a phenyl group or4-methylphenyl group; or a C1 to C12 alkoxy group such as a methoxygroup, ethoxy group, isopropoxy group or t-butoxy group.

Specific examples of the group represented by the aforementioned formula—Si(R⁵¹)R⁶¹)(R⁷¹ include —Si(CH₃)₃, —Si(C₂H₅)₃, —Si(CH₃)₂(Ph), —Si(Ph)₃,—Si(t-C₄H₉)(CH₃)₂, —Si(OCH₃)₃, —Si(OC₂H₅)₃ and —Si(OCH₃)₂CH₃.

Among these, R⁰ is preferably an organic group, and particularlypreferably a C1 to C12 haloalkyl group.

Z represents an optionally substituted aryl group, an optionallysubstituted heterocyclic group, an optionally substituted alkyl group,an optionally substituted alkenyl group or an optionally substitutedalkynyl group.

Specific examples of the optionally substituted aryl group and theoptionally substituted heterocyclic group include the same groups asthose indicated as specific examples of R⁰. Specific examples of analkyl group of the optionally substituted alkyl group, alkenyl group ofthe optionally substituted alkenyl group, and alkynyl group of theoptionally substituted alkynyl group include the same groups as thoseindicated as specific examples of R⁰. There are no particularlimitations on these substituents provided that they are within achemically allowable range, and specific examples thereof include thesame substituents as those indicated as examples of substituents oforganic groups of R⁰.

Specific examples of the substituted alkyl group include a chloromethylgroup, 2-chloroethyl group, trifluoromethyl group, 2,2,2-trifluoroethylgroup, methoxymethyl group and methylthiomethyl group.

Specific examples of the substituted alkenyl group include a2-chloroethenyl group, 2-fluoroethenyl group, 3,3,3-trifluoro-1-pentenylgroup, 1,2,2-trifluoroethenyl group, 2,3,3-trifluoro-2-propenyl group,2,3,3-triiodo-2-propenyl group and 2-methoxyethenyl group.

Specific examples of the substituted alkynyl group include a2-chloroethynyl group, 2-fluoroethynyl group, 3-fluoro-1-propynyl group,3,3,3-trifluoro-1-propynyl group, 3-fluoro-2-propynyl group and3-iodo-2-propynyl group.

Among these, Z is preferably an optionally substituted aryl group oroptionally substituted heterocyclic group, and is particularlypreferably an optionally substituted phenyl group or an optionallysubstituted 5-membered or 6-membered heterocyclic group containing atleast one heteroatom selected from the group consisting of a nitrogenatom, oxygen atom and sulfur atom.

Specific examples of the optionally substituted aryl group or theoptionally substituted heterocyclic group of the aforementioned Zinclude, but are not limited to, the following (Z-1) to (Z-32).

In the aforementioned formulas, r represents a halogen atom such as afluorine atom, chlorine atom or bromine atom; cyano group; nitro group;a C1 to C6 alkyl group such as a methyl group or ethyl group; a C1 to C6haloalkyl group such as a trifluoromethyl group or pentafluoroethylgroup; a C₃ to C₈ cycloalkyl group such as a cyclopropyl group,cyclopentyl group or cyclohexyl group; a C2 to C6 alkenyl group such asa vinyl group or propenyl group; a C2 to C6 alkynyl group such as anethynyl group or propargyl group; hydroxyl group; a C1 to C6 alkoxygroup such as a methoxy group, ethoxy group or i-propoxy group; anoptionally substituted aryloxy group such as a phenoxy group or4-methylphenoxy group; mercapto group; a C1 to C6 alkylthio group suchas a methylthio group or ethylthio group; a C1 to C6 alkylsulfinyl groupsuch as a methylsulfinyl group or ethylsulfinyl group; a C1 to C6alkylsulfonyl group such as a methylsulfonyl group or ethylsulfonylgroup; an optionally substituted arylthio group such as a phenylthiogroup or 4-chlorophenylthio group; an optionally substitutedarylsulfonyl group such as a phenylsulfonyl group or4-methylphenylsulfonyl group; a C1 to C6 alkylsulfonyloxy group such asa methylsulfonyloxy group or ethylsulfonyloxy group; an optionallysubstituted arylsulfonyloxy group such as a phenylsulfonyloxy group or2-chlorophenylsulfonyloxy group; a C1 to C6 alkoxycarbonyl group such asa methoxycarbonyl group or ethoxycarbonyl group; acyl group such as aformyl group, acetyl group, propionyl group or benzoyl group; anoptionally substituted aminocarbonyl group such as an aminocarbonylgroup, N-methylaminocarbonyl group, N-phenylaminocarbonyl group orN,N-dimethylaminocarbonyl group; or a substituted aminothiocarbonylgroup such as an N-methylaminothiocarbonyl group orN-phenylaminothiocarbonyl group. Among these, r preferably represents ahalogen atom, a C1 to C6 alkyl group or a C1 to C6 haloalkyl group.

In addition, in the aforementioned formula, examples of r′ include thesame groups as those indicated as examples of r (except halogen atoms).

m0 represents an integer of 0 to 5, m1 represents an integer of 0 to 4,m2 represents an integer of 0 to 3, m3 represents an integer of 0 to 2,and m4 represents an integer of 0 or 1. A plurality of r may be the sameor different when m0 to m3 represent an integer of 2 or more,respectively.

R³ represents a hydrogen atom, an optionally substituted aryl group, anoptionally substituted heterocyclic group, an optionally substitutedalkyl group, an optionally substituted alkenyl group, an optionallysubstituted alkynyl group or an acyl group. Specific examples of theoptionally substituted aryl group, the optionally substitutedheterocyclic group, the optionally substituted alkyl group, theoptionally substituted alkenyl group and the optionally substitutedalkynyl group of R³ are the same as the above-described examples citedas examples of Z.

Specific examples of the acyl group of R³ include an acetyl group,propionyl group, butyryl group, pivaloyl group, benzoyl group or thelike.

Q represents a group represented by formula (I′).

In formula (I′), Y represents a nitro group, hydroxyl group, mercaptogroup, halogen atom, an optionally substituted amino group or organicgroup.

Specific examples of the halogen atom, an optionally substituted aminogroup and organic group include the same groups as those indicated asspecific examples of halogen atoms, an optionally substituted aminogroup and organic groups of R⁰.

n represents an integer of 0 to 3, preferably represents 0, and aplurality of Y may be identical to or different from each other when nis 2 or more.

In addition, in the case of two adjacent Y, the two Y together may forma ring, and may form a 4-membered to 6-membered ring together with atomsrespectively bonded by the two Y by forming, for example, —CH₂CH₂CH₂—,—CH₂CH₂O—, —CH₂OCH₂—, —OCH₂O—, —CH₂CH₂S—, —CH₂SCH₂—, —SCH₂S—,—CH₂CH₂CH₂CH₂—, —CH₂CH₂CH₂O—, —CH₂CH₂OCH₂—, —CH₂OCH₂O—, —OCH₂CH₂O—,—OCH₂CH₂S—, —SCH₂CH₂S—, —OCH═N— or —SCH═N—.

In addition, the hydrogen atoms bonded to each atom that foams a ring atthis time may be substituted by a substituent T, and in the case ofbeing simultaneously substituted by two or more T, each T may be thesame or different.

Here, examples of T include a cyano group, nitro group, formyl group,halogen atom, a C1 to C6 alkyl group, a C1 to C6 alkoxy group, a C3 toC8 cycloalkyl group, a C3 to C8 cycloalkyloxy group, a C3 to C8cycloalkyl C1 to C6 alkyl group, a C3 to C8 cycloalkyl C1 to C6 alkoxygroup, a C2 to C6 alkenyloxy group, a C1 to C6 haloalkyl group, a C1 toC6 haloalkoxy group, a C2 to C6 haloalkenyloxy group, a C1 to C6alkoxycarbonyl group and an optionally substituted phenyl group.Specific examples thereof include the same groups as those indicated asexamples of the substituents of heterocyclic group of R⁰.

Among these, in the present invention, Y preferably represents a halogenatom or a C1 to C6 haloalkyl group.

D represents a 5-membered to 8-membered hydrocarbon ring group orheterocyclic group not having or having a substituent other thansubstituent X.

There are no particular limitations on the substituent other thansubstituent X provided that the substituent is chemically allowed, andexamples thereof include the same as those indicated for theaforementioned r.

X represents a group represented by the following formula (II-1) or(II-2).

In formula (II-1), R¹ and R² respectively and independently represent ahydrogen atom, nitro group, hydroxyl group, mercapto group, anoptionally substituted amino group or organic group.

Specific examples of the optionally substituted amino group and organicgroup of R¹ and R² include the same as those indicated as specificexamples of the optionally substituted amino group and organic group ofthe aforementioned R⁰.

R¹ and R¹ may bond together to form a 3-membered to 8-membered ring.Moreover, R¹ or R² may bond to A to form a 5-membered to 8-memberedring. In addition, the 3-membered to 8-membered ring and the 5-memberedto 8-membered ring may have a substituent such as an alkyl group such asa methyl group or ethyl group; a halogen atom such as a fluorine atom orchlorine atom; an oxo group (═O); or an alkoxy group such as a methoxygroup or ethoxy group.

In formula (II-2), W represents an oxygen atom or sulfur atom.

R¹¹ represents a hydrogen atom, mercapto group, an optionallysubstituted amino group or organic group. Specific examples of theoptionally substituted amino group and organic group of R¹¹ are the sameas those indicated as specific examples of the optionally substitutedamino group and organic group of the aforementioned R⁰. Among these, anoptionally substituted C1 to C12 alkyl group, an optionally substitutedC1 to C12 alkoxy group, alkylamino group, an optionally substituted arylgroup, a C1 to C12 alkyl group substituted with an optionallysubstituted heterocycle, and an optionally substituted arylamino groupare preferable.

In the aforementioned formula (I′), X is preferably represented byformula (II-1). R¹ is preferably a group represented by the followingformula (III):

In formula (III), R¹³⁰ represents a hydrogen atom, hydroxyl group,mercapto group, halogen atom, an optionally substituted amino group ororganic group, and more preferably a hydrogen atom, an optionallysubstituted amino group or organic group. W represents an oxygen atom orsulfur atom, and more preferably oxygen atom. Namely, a grouprepresented by the following formula is more preferable.

(in the formula, R¹³⁰ has the same meaning as described above).

Specific examples of the halogen atom, an optionally substituted aminogroup and organic group of R¹³⁰ are the same as those indicated asspecific examples of the halogen atom, an optionally substituted aminogroup and organic group of the aforementioned R⁰. Among these, R¹³⁰ ispreferably a C1 to C12 alkyl group, a C1 to C12 alkyl group substitutedwith a C1 to C12 alkoxy group, cyano group, acyl group, an optionallysubstituted aryl group or an optionally substituted heterocyclic group,an optionally substituted heterocyclic group, a C3 to C12 cycloalkylgroup, or an optionally substituted C3 to C12 cycloalkenyl group.

In formula (I′), A represents a carbon atom or nitrogen atom, and in thecase where A is a carbon atom and does not have a substituentrepresented by Y on the carbon atom, a hydrogen atom bonds thereto or Aforms a ring by bonding with R¹ or R² as defined below.

n1 represents an integer of 0 to 2. Two X may be identical to ordifferent from each other when n1 is 2.

In the aforementioned formula (I), Q is preferably represented by anyone of the groups represented by the following formulas:

Among these, Q is particularly preferably represented by any one of thegroups represented by the following formulas.

In the above formulas, A, Y, n, X and n1 are the same as previouslydefined, and X, a hydrogen atom or a substituent other than X is bondedto the saturated nitrogen atom.

2) Production Method of Nitrogen-containing Compound or Salt Thereof.

A compound represented by formula (I″), which is an example of thenitrogen-containing compound of the present invention, for example, canbe produced according to the method indicated below. In formula (I″)above, R⁰, Z, Y, n, D, X, n1 and A are the same as previously defined.

(in the formulas, R⁰, Z, Y, n, D, X, n1 and A are the same as previouslydefined, and J represents a halogen atom.)

Namely, a compound represented by formula (VI) is first obtained byallowing a halogenating agent to act on a compound represented byformula (V).

Examples of the halogenating agent used include N-halogenosuccinic acidimides such as N-chlorosuccinic acid imide or N-bromosuccinic acidimide; alkaline metal hypohalogenites such as sodium hypochlorite,hypohalogenous acid esters such as hypochlorous acid t-butyl ester; andsingle substance of halogens such as chlorine gas.

The halogenating agent is normally used at 1 to 10 equivalents based onthe compound represented by formula (V).

This reaction is preferably carried out in a solvent. There are noparticular restrictions on the solvent used provided that it is inert inthe reaction. Examples of the solvent used include aromatic hydrocarbonssuch as benzene, toluene or xylene; aliphatic hydrocarbons such ashexane or heptane; alicyclic hydrocarbons such as cyclohexane; aromatichalogenated hydrocarbons such as chlorobenzene or dichlorobenzene;aliphatic halogenated hydrocarbons such as dichloromethane, chloroform,carbon tetrachloride, 1,2-dichloroethane, 1,1,1-trichloroethane,trichloroethylene or tetrachloroethylene; ethers such as diethyl ether,1,2-dimethoxyethane, tetrahydrofuran or 1,4-dioxane; esters such asethyl acetate or ethyl propionate; amides such as N,N-dimethylformamide,N,N-dimethylacetoamide or N-methyl-2-pyrrolidone; alcohols such asmethanol, ethanol or ethylene glycol; carboxylic acids such as aceticacid or propionic acid; acetonitrile; and, water.

One type of these solvents can be used or two or more types thereof canbe used as a mixture.

The reaction temperature is normally within a temperature range of −60°C. to the reflux temperature of the reaction mixture.

The resulting compound represented by formula (VI) can normally besupplied to the next reaction without isolating.

Next, after allowing a base to act on the compound represented byformula (VI), a compound represented by formula (VII) can be obtained byallowing a compound represented by formula (iii) to act on the compoundrepresented by formula (IV).

Examples of the base acting on the compound represented by formula (VI)include alkaline metal hydroxides such as sodium hydroxide or potassiumhydroxide; alkaline metal carbonates such as sodium carbonate orpotassium carbonate; alkaline metal bicarbonates such as sodiumbicarbonate or potassium bicarbonate; and, organic bases such astriethylamine, imidazole or 1,8-diazabicyclo[5.4.0]-7-undecene.

The base is normally used at 1 to 5 equivalents based on the compoundrepresented by formula (VI).

This reaction is preferably carried out in a solvent. There are noparticular restrictions on the solvent used provided that it is inert inthe reaction, and examples thereof are the same as those used in thereaction to obtain the compound represented by formula (VI).

The reaction temperature is normally within a temperature range of −60°C. to the reflux temperature of the reaction mixture.

Moreover, the compound represented by formula (I″) can be contained byacting a strong base such as lithium aluminium hydroxide, lithiumdiisopropyl amide, lithium hexamethyl disilane or the like on thecompound represented by formula (VII).

When acting the strong base on the compound represented by formula(VII), solvents such as diethyl ether, tetrahydrofuran,tetrahydrofuran-hexane or the like can be used. The temperature when thestrong base acts on the compound represented by formula (VII) ispreferably −20° C. or more. The amount of the strong base is normally 1to 3 equivalents with respect to the compound represented by formula(VII).

The compound represented by formula (I) can be obtained by substitutionof OR³ for OH in the compound represented using a well-known method. Forexample, a method of performing a dehydrohalogenation reaction using ahalide of R³, which is represented by formula R³J (J represents ahalogen atom) can be used.

There are no particular limitations on salts of compounds represented byformula (I) provided that they are horticulturally and agriculturallyallowable salts. Examples of the salts of the compounds represented byformula (I) include salts of inorganic acids such as hydrochlorides,nitrates, sulfates and phosphates; and, salts of organic acids such asacetic acid, propionic acid or lactic acid.

A salt of a compound represented by formula (I) can be produced by, forexample, allowing an inorganic acid or organic acid to act on thecompound represented by formula (I).

After the reactions are completed, an ordinary post-treatment procedurecan be carried out. A target compound can be purified by a known methodsuch as distillation, recrystallization, or column chromatography, ifneeded, to isolate the target compound.

The structure of the target compound can be identified and confirmed bya known analysis such as elementary analysis, NMR spectroscopy, IRspectroscopy or mass spectroscopy.

A nitrogen-containing compound according to the present invention, orsalt thereof (to be referred to as a compound according to the presentinvention), obtained in the manner described above can be used tocontrol agriculturally harmful organisms, sanitary insect pests, storedgrain insect pests, clothing insect pests, household insect pests andthe like, and has adult insecticidal, nymph insecticidal, larvalinsecticidal and ovicidal action.

Thus, as will be described subsequently, the compound according to thepresent invention is useful as an active ingredient of a pest controlagent.

Furthermore, among the compounds according to the present invention,there are those that demonstrate antimicrobial activity, herbicidalactivity or plant growth regulatory action. In addition, the compoundsaccording to the present invention can also be used as an antifoulingagent to prevent adhesion of marine organisms to objects in contact withwater such as ship bottoms or fishnets. In addition, some intermediatesof the compounds according to the present invention also demonstrateinsecticidal and/or miticidal activity.

3) Insecticide, Miticide, Sanitary Insect Pest Control Agent or HarmfulOrganism Control Agent

The insecticide, miticide, sanitary insect pest control agent or harmfulorganism control agent according to the present invention contains as anactive ingredient thereof at least one type of the nitrogen-containingheterocyclic compound or salt thereof of the aforementioned first aspectof the present invention. In the present invention, an insecticide,miticide or sanitary insect pest control agent is preferable.

The insecticide, miticide, sanitary insect pest control agent or harmfulorganism control agent according to the present invention can be used tocontrol agriculturally harmful organisms, sanitary insect pests, storedgrain insect pests, clothing insect pests, household insect pests andthe like, and has adult insecticidal, nymph insecticidal, larvalinsecticidal and ovicidal action.

The insecticide, miticed, sanirary insect pest control agent or harmfulorganism control agent according to the present invention demonstratesuperior control effects against harmful organisms such as orderOrthoptera pests, order Thysanoptera pests, order Hemiptera pests, orderColeoptera pests, order Diptera pests, order Lepidoptera pests, orderHymenoptera pests, order Collembola pests, order Zygentoma pests, orderBlattodea pests, order Isoptera pests, order Psocoptera pests, orderMallophaga pests, order Phthiraptera pests, plant parasitic mites, plantparasitic nematodes, plant parasitic mollusks, and other harmfulanimals, nuisance animals, sanitary insect pests and parasites. Examplesof such harmful organisms include the biological species indicatedbelow.

Examples of the order Orthoptera pests include Ruspolia lineosa of thefamily Tettigoniidae, Teleogryllus emma of the family Gryllidae,Grylloptalpa orientalis of the family Gryllotalpidae, Oxya hylaintricate, Locusta migratoria or Melanoplus sanguinipes of the familyAcrididae, Attractomorpha lata of the family Pyrgomorphidae, andEuscyrtus japonicus of the family Eneopteridae.

Examples of the order Thysanoptera pests include Frankliniella intonsa,Frankliniella occidentalis, Scirtothrips dorsalis, Thrips palmi orThrips tabaci of the family Thripidae, and Ponticulothrips diospyrosi orHaplothrips aculeatus of the family Phlaeothripidae.

Examples of the order Hemiptera pests include Mogannia minute of thefamily Cicadidae, Aphrophora intermedia of the family Aphrophoridae,Machaerotypus sibiricus of the family Membracidae, Arboridia apicalis,Empoasca onukii, Nephotettix cincticeps or Recilia dorsalis of thefamily Cicadellidae, Pentastiridius apicalis of the family Cixiidae,Laodelphax striatellus, Nilaparvata lugens or Sogatella furcifera of thefamily Delphacidae, Nisia nervosa of the family Meenoplidae, Kamendakasaccharivora of the family Derbidae, Achilus flammeus of the familyAchilidae, Orosanga japonicus of the family Udoteaceae, Mimophantiamaritima of the family Flatidae, Cacopsylla pyrisuga of the familyPsyllidae, Calophya mangiferae of the family Calophyidae, Daktulosphairavitifoliae of the family Phylloxera, Adelges iaricis or Adelges tsugaeof the family Adelgidae, Acyrthosiphon pisum, Aphis gossypii, Aphisspiraecola, Lipaphis erysimi, Myzus persicae, Schizaphis graninum orRhopalospiphum padi of the family Aphididae, Aleurocanthus spiniferus,Bemisia tabaci, Bemisia argentifolii or Trialeurodes vaporariorum of thefamily Aleyrodidae,

Drosicha corpulenta or Icerya purchasi of the family Margarodidae,Dysmicoccus brevipes, Planococcus citri or Pseudococcus comstocki of thefamily Pseudococcidae, Ceroplastes ceriferus of the family Coccidae,Aclerda takahashii of the family Aclerididae, Aonidiella aurantii,Diaspidiotus perniciosus or Unaspis yanonensis of the familyDiaspididae, Lygus hesperus or Trigonotylus caelestialium of the familyMiridae, Stephanitis pyrioides or Stephanitis nashi of the familyTingidae, Eysarcoris aeneus, Lagynotomus elongatus, Nezara viridula orPlautia crossota of the family Pentatomidae, Megacopta cribraria of thefamily Plataspidae, Cavelerius saccharivorus of the family Lygaeidae,Malcus japonicus of the family Malcidae, Dysdercus cingulatus of thefamily Pyrrhocoridae, Leptocorisa acuta or Leptocorisa chinensis of thefamily Alydidae, Anacanthocoris striicornis of the family Coreidae,Rhopalus maculatus of the family Rhopalidae, and Cimex lectularis of thefamily Cimicidae.

Examples of the order Coleoptera pests include Anomara cuprea, Anomararufocuprea, Popillia japonica or Oryctes rhinoceros of the familyScarabaeidae, Agriotes ogurae, Melanotus okinawensis or Melanotusfortnumi fortnumi of the family Rhynchophoridae, Anthrenus verbasci ofthe family Dermestidae, Heterobostrychus hamatipennis of the familyBostrychidae, Stegobium paniceum of the family Anobiidae, Pitinusclavipes of the family Ptinidae, Tenebroides manritanicus of the familyTrogossitidae, Necrobia rufipes of the family Cleridae, Carpophilushemipterus of the family Nitidulidae, Ahasverus advena of the familySilvanidae, Cryptolestes ferrugineus of the family Laemophloeidae,Epilachna varivestis or Henosepilachna vigintioctopunctata of the familyCoccinellidae, Tenebrio molitor or Tribolium castaneum of the familyTenebrionidae, Epicauta gorhami of the family Meloidae, Anoplophoraglabripennis, Xylotrechus pyrrhoderus or Monochamus alternatus of thefamily Cerambycidae, Callosobruchus chinensis of the family Bruchidae,Leptinotarsa decemlineata, Diabrotica virgifera, Phaedon brassicae orPhyllotreta striolata of the family Chrysomelidae, Cylas formicarius ofthe family Brentidae, Hypera postica, Listroderes costirostris orEuscepes postfasciatus of the family Curculionidae, Echinocnemusbipunctatus or Lissorhoptus oryzophilus of the family Erirhinidae,Sitophilus zeamais or Sphenophrus venatus of the family Rhynchophoridae,Tomicus piniperda of the family Scolytidae, Crossotarsus niponicus ofthe family Platypodidae, and Lyctus brunneus of the family Lyctidae.

Examples of the order Diptera pests include Tipula aino of the familyTipulidae, Plecia nearctica of the family Bibionidae, Exechiashiitakevora of the family Mycetophilidae, Pnyxia scabiei of the familySciaridae, Asphondylia yushimai or Mayetiola destructor of the familyCecidomyiidae, Aedes aegypti or Culex pipiens pallens of the familyCulicidae, Simulium takahashii of the family Simuliidae, Chironomusoryzae of the family Chironomidae, Chrysops suavis or Tabanus trigonusof the family Tabanidae, Eumerus strigatus of the family Syrphidae,Bactrocera dorsalis, Euphranta japonica or Ceratitis capitata of thefamily Tephritidae, Liriomyza trifolii or Chromatomyia horticola of thefamily Agromyzidae, Meromyza nigriventris of the family Chloropidae,Drosophila suzukii or Drosophila melanogaster of the familyDrosophilidae, Hydrellia griseola of the family Ephydridae, Hippoboscaequina of the family Hippoboscidae, Parallelpmma sasakawae of the familyScathophagidae, Delia antiqua or Delia platura of the familyAnthomyiidae, Fannia canicularis of the family Fanniidae, Muscadomestica or Stomoxys calcitrans of the family Muscidae, Sarcophagaperegrina of the family Sarcophagidae, Gasterophilus intestinalis of thefamily Gasterophilidae, Hypoderma lineatum of the family Hypodermatidae,and Oestrus ovis of the family Oestridae.

Examples of the order Lepidoptera pests include Endoclita excrescens ofthe family Hepialidae, Antispila ampelopsia of the family Heliozelidae,Zeuzera leuconotum of the family Cossidae, Archips fuscocupreanus,Adoxophyes orana fasciata, Grapholita molesta, Homona magnanima,Leguminivora glycinivorella or Cydia pomonella of the familyTortricidae, Eupoecilia ambiguella of the family Cochylidae, Bambalinasp. or Eumeta minuscula of the family Psychidae, Nemapogon granella orTinea translucens of the family Tineidae, Bucculatrix pyrivorella of thefamily Bucculatricidae, Lyonetia clerkella of the family Lyonetiidae,Caloptilia theivora or Phyllonorycter ringoniella of the familyGracillariidae, Phyllocnistis citrella of the family Phyllocnistidae,Acrolepiopsis sapporensis of the family Acrolepiidae, Plutellaxylostella or Yponomeuta orientalis of the family Yponomeutidae,Argyresthia conjugella of the family Argyresthiidae, Nokona regalis ofthe family Sesiidae, Phthorimaea operculella, Sitotroga cerealella orPectinophora gossypiella of the family Gelechiidae, Carposina sasakii ofthe family Carposinidae, Illiberis pruni of the family Zygaenidae,Monema flavescens of the family Limacodidae, Ancylolomia japonica, Chilosuppressalis, Cnaphalocrocis medinalis, Ostrinia furnacalis or Ostrinianubilalis of the family Crambidae, Cadra cautella or Galleria mellonellaof the family Pyralidae, Nippoptilia vitis of the family Pterophoridae,Papilio xuthus of the family Papilionidae, Pieris rapae of the familyPieridae, Parnara guttata guttata of the family Hesperiidae, Ascotisselenaria of the family Geometridae, Dendrolimus spectabilis orMalacosoma neustrium testaceum of the family Lasiocampidae, Agriusconvulvuli of the family Sphingidae, Arna pseudoconspersa or Lymantriadispar of the family Lymantriidae, Hyphantria cunea of the familyArctiidae, and Agrotis ipsilon, Autographa nigrisigna, Helicoverpaarmigera, Helicoverpa zea, Heliothis virescens, Spodoptera exigua orSpodoptera litura of the family Noctuidae.

Examples of the order Hymenoptera pests include Arge pagana of thefamily Argidae, Apethymus kuri or Athalia rosae ruficornis of the familyTenthredinidae, Dryocosmus kuriphilus of the family Cynipidae, Vespasimillima xanthoptera of the family Vespidae, Solenopsis invicta of thefamily Formicidae, and Megachile nipponica of the family Megachilidae.

Examples of the order Collembola pests include Bourletiella hortensis ofthe family Sminthuridae.

Examples of the order Zygentoma pests include Lepisma saccharina orCtenolepisma villosa of the family Lepismatidae.

Examples of the order Blattodea pests include Periplaneta americana ofthe family Blattidae, and Blattela germanica of the family Blattellidae.

Examples of the order Isoptera pests include Incisitermes minor of thefamily Kalotermitidae, Coptotermes formosanus of the familyRhinotermitidae, and Odontotermes formosanus of the family Termitidae.

Examples of the order Psocoptera pests include Trogium pulsatorium ofthe family Trogiidae, and Liposcelis corrodens of the familyLiposcelidae.

Examples of the order Mallophaga pests include Menopon gallinae of thefamily Menoponidae, and Damalinia bovis of the family Gyropidae.

Examples of the order Phthiraptera pests include Haematopinus suis ofthe family Haematopinmidae, Pediculus humanus of the family Pediculidae,Linognathus setosus of the family Linognathidae, and Pediculus pubis ofthe family Pthiridae.

Examples of plant parasitic mites include Penthaleus major of the familyEupodidae, Phytonemus pallidus or Polyphagotarsonemus latus of thefamily Tarsonemidae, Siteroptes sp. of the family Pyemotidae,Brevipalpus lewisi of the family Tenuipalpidae, Tuckerella pavoniformisof the family Tuckerellidae, Eotetranychus boreus, Panonychus citri,Panonychus ulmi, Tetranychus urticae or Tetranychus kanzawai of thefamily Tetranychidae, Trisetacus pini of the family Nalepellidae,Aculops pelekassi, Epitrimerus pyri or Phyllocoptruta oleivora of thefamily Eriophyidae, Diptacus crenatae of the family Diptilomiopidae, andAleuroglyphus ovatus, Tyrophagus putrescentiae or Rhizoglyphus robini ofthe family Acaridae.

Examples of plant parasitic nematodes include Xiphinema index of thefamily Longidoridae, Paratrichodorus minor of the family Trichodoridae,Rhabditella sp. of the family Rhabditidae, Aglenchus sp. of the familyTylenchidae, Cephalenchus sp. of the family Tylodoridae, Nothotylenchusacris or Ditylenchus destructor of the family Anguinidae, Rotylenchulusreniformis or Helicotylenchus dihystera of the family Hoplolaimidae,Paratylenchus curvigtatus of the family Paratylenchidae, Meloidogyneincognita or Meloidogyne hapla of the family Meloidogynidae, Globoderarostochiensis or Heterodera glycines of the family Heteroderidae,Tylenchorhynchus claytoni of the family Tylenchorhynchidae, Psilenchussp. of the family Tylenchidae, Criconemoides sp. of the familyCriconematidae, Tylenchulus semipenetrans of the family Tylenchulidae,Sphaeronema camelliae of the family Sphaeronematinae, Sphaeronemacamelliae, Radopholus citrophilus, Radopholus similis, Nacobbusaberrans, Pratylenchus penetrans or Pratylenchus coffeae of the familyPratylenchidae, Iotonchium ungulatum of the family Iotonchiidae,Aphelenchus avenae of the family Aphelenchoididae, Aphelenchoidesbesseyi or Aphelenchoides fragariae of the family Aphelenchoididae, andBursaphelenchus xylophilus of the family Parasitaphelenchidae.

Examples of plant parasitic mollusks include Pomacea canaliculata of thefamily Helicodiscidae, Leavicaulis alte of the family Veronicellidae,Achatina fulica of the family Achatinidae, Meghimatium bilineatum of thefamily Philomycidae, Succinea lauta of the family Succineacea, Discuspauper of the family Discidae, Zonitoides yessoensis of the familyZonitidae, Limax flavus or Deroceras reticulatum of the familyLimacidae, Parakeliella harimensis of the family Helicarionidae, andAcusta despecta sieboldiana or Bradybaena similaris of the familyBradybaenidae.

Examples of other harmful animals, nuisance animals, sanitary insectpests and parasites include members of the order Parasitiformes such asOrnithonyssus sylvialum of the family Macronyssidae, Varroa jacobsoni ofthe family Varroidae, Dermanyssus gallinae of the family Dermanyssidae,Ornithonyssus sylvialum of the family Macronyssidae, Boophilusmicroplus, Rhipicephalus sanguineus or Haemaphysalis longicornis of thefamily Ixodidae, or Sarcoptes scabiei of the family Sarcoptidae, membersof the order Isopoda such as Armadillidium vulgare of the familyArmadillidiidae, members of the order Isopoda such as Armadillidiumvulgare of the family Porcellionidae, Chilopoda class pests such asThereuonema tuberculata of the order Scutigeromorpha, familyScutigeridae or Scolopendra subspinipes of the order Scolopendromorpha,Helminthomorpha class pests such as Oxidus gracilis of the orderPolydesmida, family Paradoxosomatidae, Theridiidae hasseltii of theorder Araneae, family Theridiidae, Chiracanthium japonicum of the orderAraneae, family Clubionidae, Androctonus crassicauda of the orderScorpiones, nematode internal parasites in the form of Ascarislumbricoides, Syphacia sp. and Wuchereria bancrofti, and flatworminternal parasites in the form of Distomum sp., Paragonimus westermanii,Metagonimus yokokawai, Schistosoma japonicum, Taenia solium,Taeniarhynchus saginatus, Echinococcus sp. and Diphyllobothrium latum.

The compounds of the present invention, the insecticides, miticides,sanitary insect pest control agents or harmful organism control agentsof the present invention also demonstrate control effects againstharmful organisms and the like as exemplified above that have acquiredresistance to existing pest control agents.

In addition, the compounds of the present invention, the insecticides,miticides, sanitary insect pest control agents or harmful organismcontrol agents of the present invention can also be used in plants thathave acquired characteristics such as pest resistance, diseaseresistance or herbicide resistance and the like through generecombination or artificial hybridization.

In addition, numerous pests such as diamondback moths, planthoppers,leafhoppers and aphids have recently developed resistance to organicphosphorous agents, carbamate agents and miticides, and problems haveoccurred regarding the inadequate effects of these chemicals, thusresulting in the desire for an effective chemical against resistantstrains of pests and mites. The compounds according to the presentinvention demonstrate superior insecticidal and miticidal effectsagainst strains of pests resistant to organic phosphorous agents,carbamate agents and pyrethroid agents, and miticide-resistant strainsof mites as well as sensitive strains of pests or mites. In addition,the harmful organism control agent according to the present inventionhas low levels of chemical damage, low toxicity with respect to fish andmammals, and is highly safe.

In the case of an actual application of the compounds of the presentinvention, the insecticides, miticides, sanitary insect pest controlagents or harmful organism control agents of the present invention,although one type or two or more types of compounds according to thepresent invention can be used as is without adding other components, onetype or two or more types of the compounds of the present invention arenormally mixed with a solid vehicle, liquid vehicle or gaseous vehicle,or impregnated into a base material such as a porous ceramic plate ornon-woven fabric, followed by the addition of a surfactant or otherauxiliary agent as necessary, and is used by formulating into a formthat can be adopted by ordinary agricultural chemicals for the purposeof use as an agricultural chemical, examples of which include wettablepowders, granules, powders, emulsions, aqueous solutions, suspensions,water-dispersible granules, flowable preparations, aerosols, sprayingagents, heat transpiration agents, smoking agents, poison bait andmicrocapsules.

In the case of using an additive or vehicle for the purpose of obtaininga solid agent, a plant-based powder such as powdered soybeans orpowdered wheat, a mineral-based fine powder such as diatomaceous earth,apatite, gypsum, talc, bentonite, pyrophyllite or clay, or an organic orinorganic compound such as sodium benzoate, urea or sodium sulfate canbe used. In the case of using for the purpose of obtaining a liquidagent, a petroleum distillate such as kerosene, xylene or solventnaphtha, or cyclohexane, cyclohexanone, dimethylformamide,dimethylsulfoxide, alcohol, acetone, methyl isobutyl ketone, mineraloil, vegetable oil, water, or the like can be used as a solvent.Examples of gaseous vehicles used in a spraying agent include butanegas, LG, dimethylether and carbon dioxide gas.

Examples of base materials of the poison bait include bait componentssuch as grains, vegetable oils, sugars, or crystalline cellulose,antioxidants such as dibutylhydroxytoluene or nordihydroguaiaretic acid,preservatives such as dehydroacetic acid, agents for preventingaccidental ingestion by children or pets such as powdered cayennepepper, and pest-attracting aromatic components such as cheese fragranceor onion fragrance.

A surfactant can be added to these preparations as necessary in order toobtain a homogeneous and stable preparation form. There are noparticular limitations on the surfactant used, and examples thereofinclude nonionic surfactants such as polyoxyethylene-added alkyl ethers,polyoxyethylene-added higher fatty acid esters, polyoxyethylene-addedsorbitan higher fatty acid esters or polyoxyethylene-addedtristyrylphenyl ethers, sulfate ester salts of polyoxyethylene-addedalkylphenyl ethers, alkyl naphthalene sulfonates, polycarboxylates,lignin sulfonates, formaldehyde condensation products of alkylnaphthalene sulfonates and copolymers such as isobutylene-maleicanhydride copolymer.

Although there are no particular limitations on the amount of activeingredient in the insecticides, miticides, sanitary insect pest controlagents or harmful organism control agents of the present invention, itis preferably 0.01 to 90% by weight and particularly preferably 0.05 to85% by weight.

In the case of using the compounds of the present invention inagricultural applications, the preparation form is in the form of awettable powder, emulsion, suspension, flowable preparation, aqueoussolution or water-dispersible granules, and can be used by dilutingthese preparations to a prescribed concentration with water to obtain asolution, suspension or emulsion, and then spraying a powder or granulesdirectly onto plants or soil.

In addition, in the case of using the compound according to the presentinvention as a harmful organism control agent for preventing disease,the preparation form thereof is in the foils of an emulsion, wettablepowder, flowable preparation, or the like, and these preparations can beapplied by diluting to a prescribed concentration with water. Inaddition, the compound according to the present invention can be useddirectly in the case where the preparation form thereof is an oilyagent, aerosol, spraying agent, poison bait or miticidal sheet.

In the case of using the compound according to the present invention asa harmful organism control agent for controlling external parasites oflivestock such as cows or pigs or pets such as dogs or cats, apreparation of the compound according to the present invention cannormally be used according to a known veterinary method.

Examples of such methods include administration in the form of a tablet,capsule, permeating liquid, feed additive, suppository or injection(intramuscular, subcutaneous, intravenous or intraperitoneal injection)in the case of aiming at systemic control, and administration byspraying, pouring or spotting an oily or aqueous liquid, or forming aresin preparation into a suitable shape such as that of a collar, eartag, or the like to attach the resin preparation to the animal in thecase of aiming at non-systemic control. In this case, the preparation isnormally used at the rate of 0.01 to 1000 mg of the compound accordingto the present invention per 1 kg of body weight of the host animal.

Although the compounds of the present invention, the insecticides,miticides, sanitary insect pest control agents or harmful organismcontrol agents of the present invention naturally demonstrates adequateeffects when used alone, it can also be mixed or used in combinationwith one type or two or more types of other miticidal agents,antimicrobial agents, insecticidal and acaricidal agents, herbicides,plant growth regulators, synergists, fertilizers, soil conditioners oranimal feeds.

In addition, in the case of using the compound according to the presentinvention as an agricultural chemical, it may be applied after mixingwith other types of herbicides, various types of insecticides,miticides, nematocides, antimicrobial agents, plant growth regulators,synergists, fertilizers or soil conditioners as necessary either duringformulation or during spraying.

By applying after mixing with other agricultural chemicals or planthormones in particular, reduced costs resulting from decreasing theamount of chemical applied, and a broader insecticidal spectrum andgreater pest control effects due to the synergistic action of the mixedchemicals, can be expected. At this time, the compound according to thepresent invention can be simultaneously combined with a plurality ofknown agricultural chemicals. Examples of types of the agriculturalchemicals used by mixing with the compound according to the presentinvention include compounds listed in the 2007 edition of the CropProtection Handbook. Specific examples thereof include, but are notlimited to, agricultural chemicals listed below using their genericnames.

Examples of active ingredient compounds of antimicrobial agents (genericname, including those for which application is currently pending)include:

anilinopyrimidine-based compounds such as mepanipyrim, pyrimethanil orcyprodinil;

pyridinamine-based compounds such as fluazinam;

azole-based compounds such as triadimefon, bitertanol, triflumizole,etaconazole, propiconazole, penconazole, flusilazole, myclobutanil,cyproconazole, tebuconazole, hexaconazole, furconazole-cis, prochloraz,metconazole, epoxiconazole, tetraconazole, oxpoconazole fumarate,sipconazole, prothioconazole, triadimenol, flutriafol, difenoconazole,fluquinconazole, fenbuconazole, bromuconazole, diniconazole,tricyclazole, probenazole, simeconazole, pefurazoate, ipconazole,imibenconazole or imazalil;

quinoxaline-based compounds such as quinomethionate;

dithiocarbamate-based compounds such as maneb, zineb, mancozeb,polycarbamate, metiram, propineb, ferbam, nabam, metam, thiram or ziram;

organic chlorine-based compounds such as fthalide, chlorothalonil orquintozene;

imidazole-based compounds such as benomyl, thiophanate-methyl,carbendazim, thiabendazole, fuberiazole or cyazofamid;

cyanoacetoamide-based compounds such as cymoxanil;

phenylamide-based compounds such as metalaxyl, metalaxyl-M, mefenoxam,oxadixyl, ofurace, benalaxyl, benalaxyl-M, furalaxyl or cyprofuram;

sulfenic acid-based compounds such as dichlofluanid;

nitrophenyl-based compounds such as dinocap;

copper-based compounds such as cupric hydroxide or oxine copper;

isoxazole-based compounds such as hymexazol;

organic phosphorous-based compounds such as fosetyl-Al, tolcofos-methyl,S-benzyl-O,O-diisopropyl phosphorothioate, O-ethyl-S,S-diphenylphosphorodithioate or aluminum ethyl hydrogen phosphonate;

N-halogenothioalkyl-based compounds such as captan, captafol or folpet;

dicarboxylmide-based compounds such as procymidone, iprodone orvinclozolin;

benzanilide-based compounds such as flutolanil, mepronil, zoxamid ortiadinil;

anilide-based compounds such as carboxin, oxycarboxin, thifluzamide,penthiopyrad, boscalid, fluopicolide, fluopyram or bixafen;

piperazine-based compounds such as triforine;

pyridine-based compounds such as pyrifenox;

carbinol-based compounds such as fenarimol or flutriafol;

piperidine-based compounds such as fenpropidine;

morpholine-based compounds such as fenpropimorph or tridemorph;

organic tin-based compounds such as fentin hydroxide or fentin acetate;

urea-based compounds such as pencycuron;

cinnamic acid-based compounds such as dimethomorph, flumorph orflumetover;

phenylcarbamate-based compounds such as diethofencarb;

cyanopyrrole-based compounds such as fludioxonil or fenpiclonil;

strobilurin-based compounds such as azoxystrobin, kresoxim-methyl,metominofen, metominostrobin, trifloxystrobin, picoxystrobin,oryzastrobin, dimoxystrobin, pyraclostrobin or fluoxastrobin;

oxazolidinone-based compounds such as famoxadone;

thiazole carboxamide-based compounds such as ethaboxam;

silyl amide-based compounds such as silthiopham;

amino acid amide carbamate-based compounds such asbenthiavalicarb-isopropyl;

imidazolidine-based compounds such as fenamidone;

hydroxyanilide-based compounds such as fenhexamid;

benzenesulfonamide-based compounds such as flusulfamide;

oxime ether-based compounds such as cyflufenamid;

phenoxyamide-based compounds such as fenoxanil;

antibiotics such as validamycin, kasugamycin or polyoxins; and,

guanidine-based compounds such as iminoctadine.

In addition, examples of other compounds include tolyfluanid,isoprothiolane, pyroquilon, diclomezine, quinoxyfen, propamocarbhydrochloride, spiroxamine, chloropicrin, dazomet, metam-sodium,nicobifen, metrafenone, UBF-307, diclocymet, proquinazid, amisulbrom,pyribencarb, mandipropamid,5-chlor-7-(4-methyl-piperidin-1-yl)-6-(2,4,6-trifluor-phenyl)-[1,2,4]thiazolo[1,5-a]pyrimidinand OK-5203.

Examples of active ingredient compounds of insecticides, miticides,nematocides or soil pest control agents that are agricultural chemicalsused in sprayed liquids (generic name, including those for whichapplication is currently pending) include:

organic phosphate ester-based compounds such as profenofos, dichlorvos,fenamiphos, fenitrothion, EPN, diazinon, chlorpyrifos-methyl, acephate,prothiofos, fosthiazate, phosphocarb, cadusafos, dislufoton,chlorpyrifos, demeton-S-methyl, dimethoate, methamidophos, isoxathion,isofenphos, ethion, etrimfos, quinalphos, dimethylvinphos, sulprofos,thiometon, vamidothion, pyraclofos, pyridaphenthion, pirimiphos-methyl,propaphos, phosalone, formothion, malathion, tetraclovinphos,chlorfenvinphos, cyanophos, trichlorfon, methidathion, phenthoate, ESP,azinphos-methyl, fenthion, heptenophos, methoxychlor, paration,monocrotophos, imicyafos, parathion-methyl, terbufos, phospamidon,phosmet or phorate;

carbamate-based compounds such as carbaryl, propoxur, aldicarb,carbofuran, thiodicarb, methomyl, oxamyl, ethiofencarb, pirimicarb,fenobucarb, carbosulfan, benfuracarb, bendiocarb, furathiocarb,isoprocarb, metolcarb, xylylcarb, XMC or fenothiocarb;

nereistoxin derivatives such as cartap, thiocyclam, bensultap orthiosultap-sodium; organic chlorine-based compounds such as dicofol,tetradifon, endosulufan, dienochloror dieldrin;

organic metal-based compounds such as fenbutatin oxide or cyhexatin;

pyrethroid-based compounds fenvalerate, permethrin, cypermethrin,deltamethrin, cyhalothrin, tefluthrin, ethofenprox, cyfluthrin,fenpropathrin, bifenthrin, flucythrinate, fluvalinate, cycloprothrin,lambda-cyhalothrin, pyrethrins, esfenvalerate, tetramethrin, resmethrin,protrifenbute, zeta-cypermethrin, acrinathrin, alpha-cypermethrin,allethrin, gamma-cyhalothrin, theta-cypermethrin, tau-fluvalinate,tralomethrin, profluthrin, beta-cypermethrin, beta-cyfluthrin,metofluthrin or phenothrin;

benzoylurea-based compounds such as diflubenzuron, chlorfluazuron,teflubenzuron, flufenoxuron, lufenuron, novaluron, triflumuron,hexaflumuron, noviflumuron, bistrifluoron or fluazuron;

juvenile hormone-like compounds such as methoprene, pyriproxyfen,fenoxycarb or diofenolan;

pyridazinone-based compounds such as pyridaben;

pyrazole-based compounds such as fenpyroximate, fipronil, tebufenpyrad,ethiprole, tolfenpyrad, acetoprole, pyrafluprole or pyriprole;

neonicotinoids such as imidacloprid, nitenpyram, acetamiprid,thiacloprid, thiamethoxam, clothianidin, dinotefuran or nithiazine; and,

hydrazine-based compounds such as tebufenozide, methoxyfenozide,chromafenozide or halofenozide.

Examples of other compounds include flonicamid, buprofezin, hexythiazox,amitraz, chlordimeform, silafluofen, triazamate, pymetrozine,pyrimidifen, chlorfenapyr, indoxacarb, acequinocyl, etoxazole,cyromazine, 1,3-dichloropropene, diafenthiuron, benclothiaz, flufenerim,pyridalyl, spirodiclofen, bifenazate, spiromesifen, spirotetramat,propargite, clofentezine, fluacrypyrim, metaflumizone, flubendiamide,cyflumetofen, chlorantraniliprole, cyenopyrafen, pyrifluquinazon,fenazaquin, amidoflumet, chlorobenzoate, sulfluramid, hydramethylnon,metaldehyde and ryanodine.

Moreover, additional examples of compounds include crystal proteintoxins produced by Bacillus thuringienses aizawai, Bacillusthuringienses kurstaki, Bacillus thuringienses israelensis, Bacillusthuringienses japonensis, Bacillus thuringienses tenebrionis or Bacillusthuringienses; microbial agricultural chemicals such as insect pathogenviral agents, insect pathogen fungal agents or nematode pathogen fungalagents; antibiotics or semi-synthetic antibiotics such as avermectin,emamectin-benzoate, milbemectin, spinosad, ivermectin or lepimectin;

naturally-occurring substances such as azadirachtin or rotenone;

cooperative agents such as piperonyl butoxide; and

repellents such as deet.

EXAMPLES

Next, the present invention will be described in more detail. However,there are no limitations on the present invention.

Example 1 Production ofN-[5-{(Z)-3-(3,5-dichlorophenyl)-4,4,4-trifluoro-1-hydroxyimino-2-butenyl]-indane-1-yl}-3-methoxybutyricacid amide (Compound No. 10)

0.5 g ofN-{5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazole-3-yl]indane-1-yl}-3-methoxybutyricacid amide was dissolved in 20 ml of tetrahydrofuran. 2 ml of 1.0 Mtetrahydrofuran solution of lithium hexamethyl disilazane was addeddropwise into the resulting solution at room temperature and stirred for30 minutes at room temperature. The resulting solution was poured intoice water, and acidized using 2N hydrochloric acid, extracted with ethylacetate, washed with saturated brine, followed by drying with anhydrousmagnesium sulfate. The solvent was distilled off under reduced pressureand the resulting residue was purified by silica gel columnchromatography (eluent: ethyl acetate/n-hexane=3/1 (volume ratio)) toobtain 0.5 g of the target compound. Yield was 100%.

¹H-NMR (CDCl₃, δ ppm) 1.27 (d, 3H), 1.78-1.88 (m, 1H), 2.59-2.70 (m,1H), 2.81-3.02 (m, 2H), 3.36 (s, 3H), 3.77-3.83 (m, 1H), 5.52 (q, 1H),6.63 (d, 1H), 6.73 (s, 1H), 7.24-7.43 (m, 6H), 8.54 (s, 1H)

Example 2 Production ofN-[5-{(Z)-3-(3,5-dichlorophenyl)-4,4,4-trifluoro-1-methoxymethoxyimino-2-butenyl}-indane-1-yl]-3-methoxybutyricacid amide (Compound No. 11)

0.5 g ofN-[5-{(Z)-3-(3,5-dichlorophenyl)-4,4,4-trifluoro-1-hydroxyimino-2-butenyl]-indane-1-yl}-3-methoxybutyricacid amide was dissolved in 10 ml of tetrahydrofuran, and 0.08 g of 60%sodium hydride was added to the resulting solution under ice-coldconditions, followed by stirring for 30 minutes at room temperature. Thetemperature was cooled again, and 0.1 g of chloromethyl methyl ether wasadded to the resulting solution, followed by stirring for one night atroom temperature. The reaction solution was poured into ice-water,extracted with ethyl acetate, washed with saturated brine, followed bydrying with anhydrous magnesium sulfate. The solvent was distilled offunder reduced pressure and the resulting residue was purified by silicagel column chromatography (eluent: ethyl acetate/n-hexane=7/3 (volumeratio)) to obtain 0.3 g of the target compound. Yield was 54%.

¹H-NMR (CDCl₃, δ ppm) 1.25 (d, 3H), 1.78-1.85 (m, 1H), 2.38-3.01 (m,5H), 3.32 (s, 3H), 3.50 (s, 3H), 3.72-3.78 (m, 1H), 5.25 (s, 2H), 5.52(q, 1H), 6.46 (d, 1H), 6.74 (s, 1H), 7.10-7.56 (m, 6H)

Example 3 Production ofN-[5-{(Z)-3-(3,5-dichlorophenyl)-4,4,4-trifluoro-1-acetyloxyimino-2-butenyl}-indane-1-yl]-3-methoxybutyricacid amide (Compound No. 12)

0.5 g ofN-[5-{(Z)-3-(3,5-dichlorophenyl)-4,4,4-trifluoro-1-hydroxyimino-2-butenyl}-indane-1-yl]-3-methoxybutyricacid amide and 0.22 g of triethylamine were dissolved in 10 ml oftetrahydrofuran, and 0.1 g of acetyl chloride was added to the resultingsolution under ice-cold conditions, followed by stirring at roomtemperature for one night. The reaction solution was poured intoice-water, extracted with ethyl acetate, washed with saturated brine,followed by drying with anhydrous magnesium sulfate. The solvent wasdistilled off under reduced pressure and the resulting residue waspurified by silica gel column chromatography (eluent: ethylacetate/n-hexane=7/3 (volume ratio)) to obtain 0.39 g of the targetcompound. Yield was 69%.

¹H-NMR (CDCl₃, δ ppm) 1.26 (d, 3H), 1.79-1.86 (m, 1H), 2.23 (s, 3H),2.40-2.49 (m, 2H), 2.61-2.69 (m, 1H), 2.88-3.18 (m, 2H), 3.33 (s, 3H),3.72-3.78 (m, 1H), 5.54 (q, 1H), 6.49 (d, 1H), 6.71 (s, 1H), 7.32-7.68(m, 6H)

The structures and physical indices of the compounds represented byformula (A), which are produced in the same manner as theabove-described Examples are shown in TABLE 1. The abbreviationsdescribed in the table have the following meanings:

Ph: phenylPy: pyridylPr: propylc: cycloHex: hexylBu-t: t-butylPr-n: n-propylPr-c: cyclopropyl

TABLE 1 Compound No. Z R⁰ (Y)_(n) R¹ R² R³ 1 3,5-Cl₂Ph CF₃ — n-Pr H H 23,5-Cl₂Ph CF₃ — CH₂CH₂(2-Py) H H 3 3,5-Cl₂Ph CF₃ — CH₂CH₂COCH₃ H H 43,5-Cl₂Ph CF₃ — CH₂CH₂OCH₃ H H 5 3,5-Cl₂Ph CF₃ — COCH₃ H H 6 3,5-Cl₂PhCF₃ — COC₂H₅ H H 7 3,5-Cl₂Ph CF₃ — COPr-n H H 8 3,5-Cl₂Ph CF₃ —COCH₂CH₂OCH₃ H H 9 3,5-Cl₂Ph CF₃ — COCH₂CH₂OCH₂CH₃ H H 10 3,5-Cl₂Ph CF₃— COCH₂CH(CH₃)OCH₃ H H 11 3,5-Cl₂Ph CF₃ — COCH₂CH(CH₃)OCH₃ H CH₂OCH₃ 123,5-Cl₂Ph CF₃ — COCH₂CH(CH₃)OCH₃ H C(═O)CH₃ 13 3,5-Cl₂Ph CF₃ —COCH₂CH(CH₃)OCH₂CH₃ H H 14 3,5-Cl₂Ph CF₃ — COCH₂CH(CH₃)OH H H 153,5-Cl₂Ph CF₃ — COCH₂CH₂OCH₂CH═CH₂ H H 16 3,5-Cl₂Ph CF₃ — COCH₂COCH₃ H H17 3,5-Cl₂Ph CF₃ — COCH₂(1,3-dioxolane-2-yl) H H 18 3,5-Cl₂Ph CF₃ —COCH₂(2-methyl-1,3- H H dioxolane-2-yl) 19 3,5-Cl₂Ph CF₃ — COCH₂(2- H Htrifluoromethyl- 1,3-dioxolane-2-yl) 20 3,5-Cl₂Ph CF₃ —COCH₂(2-methyl-1,3- H H dioxane-2-yl) 21 3,5-Cl₂Ph CF₃ — COCH₂CH₂(1,3- HH dioxolane-2-yl) 22 3,5-Cl₂Ph CF₃ — COCH₂CH₂(2-methyl- H H1,3-dioxolane-2-yl) 23 3,5-Cl₂Ph CF₃ — CO(tetrahydropyran- H H 4-yl) 243,5-Cl₂Ph CF₃ — CO(2,6-dimethyl-4H- H H pyran-4-one-3-yl) 25 3,5-Cl₂PhCF₃ — COCH₂CH₂CN H H 26 3,5-Cl₂Ph CF₃ — COCH₂CH₂Ph H H 27 3,5-Cl₂Ph CF₃— COCH₂CH₂(1,2,4- H H triazole-1-yl) 28 3,5-Cl₂Ph CF₃ —COCH₂CH₂(pyrazole-1- H H yl) 29 3-CF₃Ph CF₃ — COC₂H₅ H H 30 3-CF₃Ph CF₃— COCH₂CH₂OCH₃ H H 31 3-CF₃Ph CF₃ — COCH₂CH(CH₃)OCH₃ H H 32 3-CF₃Ph CF₃— COCH₂(2-methyl-1,3- H H dioxolane-2-yl) 33 3-CF₃Ph CF₃ — COCH₂CH₂CN HH 34 3,5-Cl₂Ph CF₃ — COPr-c H H 35 3,5-Cl₂Ph CF₃ — COHex-c H H 362-F-3-CF₃Ph CF₃ — COC₂H₅ H H 37 2-F-3-CF₃Ph CF₃ — COCH₂CH₂OCH₃ H H 383-CF₃-4-ClPh CF₃ — COC₂H₅ H H 39 3-CF₃-4-ClPh CF₃ — COCH₂CH₂OCH₃ H H 403-CF₃-4-ClPh CF₃ — COCH₂CH(CH₃)OCH₃ H H 41 3,5-Cl₂Ph CF₃ — CSC₂H₅ H H 423,5-Cl₂Ph CF₃ — 2-cyclohexenone-3- H H yl 43 3,5-Cl₂Ph CF₃ —CH₂(4-methyl-1,3- H H dioxolene-2-one-5-yl) 44 3,5-Cl₂Ph CF₃ —CH₂(4-methyl-1,3- CH₂(4-methyl- H dioxolene-2-one-5- 1,3-dioxolene- yl)2-one-5-yl) 45 3,5-Cl₂Ph CF₃ — COC₂H₅ CH₃ H 46 3,5-Cl₂Ph CF₃ — H H H 473-CF₃Ph CF₃ — H H H 48 2-F-3-CF₃Ph CF₃ — H H H 49 3-CF₃-4-ClPh CF₃ — H HH 50 3,5-Cl₂Ph CF₃ 4-F COC₂H₅ H H 51 3,5-Cl₂Ph CF₃ 4-Cl COC₂H₅ H H 523,5-Cl₂Ph CF₃ 4-CH₃ COC₂H₅ H H 53 3,5-Cl₂Ph CF₃ 4-CF₃ COC₂H₅ H H 543,5-Cl₂Ph CF₃ 4-CH₂OCH₃ COC₂H₅ H H 55 3,5-Cl₂Ph CF₃ 4-NO₂ COC₂H₅ H H 563,5-Cl₂Ph CF₃ 4-OH COC₂H₅ H H 57 3,5-Cl₂Ph CF₃ 4-OCH₃ COC₂H₅ H H 583,5-Cl₂Ph CF₃ 4-OCF₃ COC₂H₅ H H 59 3,5-Cl₂Ph CF₃ 4-OCH₂COCH₃ COC₂H₅ H H60 3,5-Cl₂Ph CF₃ 4-SH COC₂H₅ H H 61 3,5-Cl₂Ph CF₃ 4-SCH₃ COC₂H₅ H H 623,5-Cl₂Ph CF₃ 4-SCF₃ COC₂H₅ H H 63 3,5-Cl₂Ph CF₃ 4-NH₂ COC₂H₅ H H 643,5-Cl₂Ph CF₃ 4-NHCH₃ COC₂H₅ H H 65 3,5-Cl₂Ph CF₃ 4-N(CH₃)₂ COC₂H₅ H H66 3,5-Cl₂Ph CF₃ 4-NHPh COC₂H₅ H H 67 3,5-Cl₂Ph CF₃ 4-NHCOCH₃ COC₂H₅ H H68 3,5-Cl₂Ph CF₃ 4-NHCO₂C₂H₅ COC₂H₅ H H 69 3,5-Cl₂Ph CF₃ 4-NHCO₂Bu-tCOC₂H₅ H H 70 3,5-Cl₂Ph CF₃ 4-NHCH₂Ph COC₂H₅ H H 71 3,5-Cl₂Ph CF₃ 7-FCOC₂H₅ H H 72 3,5-Cl₂Ph NO₂ — COC₂H₅ H H 73 3,5-Cl₂Ph OH — COC₂H₅ H H 743,5-Cl₂Ph OMe — COC₂H₅ H H 75 3,5-Cl₂Ph OCF₃ — COC₂H₅ H H 76 3,5-Cl₂PhSH — COC₂H₅ H H 77 3,5-Cl₂Ph SCF₃ — COC₂H₅ H H 78 3,5-Cl₂Ph Cl — COC₂H₅H H 79 3,5-Cl₂Ph NH₂ — COC₂H₅ H H 80 3,5-Cl₂Ph NHCOCH₃ — COC₂H₅ H H 813,5-Cl₂Ph NHCO₂C₂H₅ — COC₂H₅ H H 82 3,5-Cl₂Ph CO₂C₂H₅ — COC₂H₅ H H 833,5-Cl₂Ph SO₂CH₃ — COC₂H₅ H H 84 3,5-Cl₂Ph SO₂CF₃ — COC₂H₅ H H 853,5-Cl₂Ph Ph — COC₂H₅ H H 86 3,5-Cl₂Ph COCH₃ — COC₂H₅ H H 87 3,5-Cl₂PhCl — COC₂H₅ H H 88 3,5-Cl₂Ph CF₂H — COC₂H₅ H H 89 3,5-Cl₂Ph CCl₃ —COC₂H₅ H H 90 3,5-Cl₂Ph CF₂Cl — COC₂H₅ H H 91 CH₃CH═CH CF₃ — COC₂H₅ H H92 Propargyl CF₃ — COC₂H₅ H H 93 CH₂═CHCH₂ CF₃ — COC₂H₅ H H 94 2-butynylCF₃ — COC₂H₅ H H 100 3,5-Cl₂Ph CF₃ — CONHCH₃ H H 101 3,5-Cl₂Ph CF₃ —CONHC₂H₅ H H 102 3,5-Cl₂Ph CF₃ — CONHPr-n H H 103 3,5-Cl₂Ph CF₃ —CONHCH₂CH₂OCH₃ H H 104 3,5-Cl₂Ph CF₃ — CONHCH₂CH₂OCH₂CH₃ H H 1053,5-Cl₂Ph CF₃ — CONHCH₂CH(CH₃)OCH₃ H H 106 3,5-Cl₂Ph CF₃ — CON(CH₃)₂ H H107 3,5-Cl₂Ph CF₃ — CONHCH₂CH₂CN H H 108 3,5-Cl₂Ph CF₃ — CONHCH₂CH₂Ph HH 109 3,5-Cl₂Ph CF₃ — CONHCH₂CH₂(1,2,4- H H triazole-1-yl) 110 3,5-Cl₂PhCF₃ — CONHCH₂CH₂(pyrazole- H H 1-yl) 111 3,5-Cl₂Ph CF₃ — CONHOH H H 1123,5-Cl₂Ph CF₃ — CONHOCH₃ H H 113 3,5-Cl₂Ph CF₃ — CONHPr-c H H 1143,5-Cl₂Ph CF₃ — CONHPh H H 115 3,5-Cl₂Ph CF₃ — CSNHCH₃ H H 116 3,5-Cl₂PhCF₃ — CO₂C₂H₅ H H 117 3,5-Cl₂Ph CF₃ — CO₂Pr-n H H 118 3,5-Cl₂Ph CF₃ —CO₂Pr-c H H 119 3,5-Cl₂Ph CF₃ — CO₂CH₂CH₂OCH₃ H H 120 3,5-Cl₂Ph CF₃ —CO₂CH₂CH₂OCH₂CH₃ H H 121 3,5-Cl₂Ph CF₃ — CO₂CH₂CH(CH₃)OCH₃ H H 1223,5-Cl₂Ph CF₃ — CO₂CH₂CH₂CN H H 123 3,5-Cl₂Ph CF₃ — CO₂CH₂CH₂Ph H H 1243,5-Cl₂Ph CF₃ — CO₂CH₂CH₂(1,2,4- H H triazole-1-yl) 125 3,5-Cl₂Ph CF₃ —CO₂CH₂CH₂(pyrazole- H H 1-yl) 126 3,5-Cl₂Ph CF₃ — CH₂CH₂CH₂CH₂ (form aring) H 127 3,5-Cl₂Ph CF₃ — C(═O)CH₂CH₂CH₂ (form a ring) H 128 3,5-Cl₂PhCF₃ — C(═O)CH₂CH₂C(═O) (form a ring) H 129 3,5-Cl₂Ph CF₃ — phthaloyl(form a ring) H 130 2,4-diCF₃- CF₃ — COCH₂CH(CH₃)OCH₃ H H pyrimidine-6-yl 131 2-CH₃S-4-CF₃- CF₃ — COCH₂CH(CH₃)OCH₃ H H pyrimidine-6- yl 1322-CH₃O-4-CF₃- CF₃ — COCH₂CH(CH₃)OCH₃ H H pyrimidine-6- yl 1332-Cl-4-CF₃- CF₃ — COCH₂CH(CH₃)OCH₃ H H pyrimidine-6- yl 134 2-Br-4-CF₃-CF₃ — COCH₂CH(CH₃)OCH₃ H H pyrimidine-6- yl 135 3,5-Cl₂Ph CF₃ —COCH₂Pr-c H H 136 3,5-Cl₂Ph CF₃ — 2-cyclopentenone-3- H H yl 1373-CF₃-4-CH₃Ph CF₃ — COCH₂CH₃ H H 138 3-CF₃-4-OCH₃Ph CF₃ — COCH₂CH₃ H H139 3-CF₃-4-CNPh CF₃ — COCH₂CH₃ H H 140 3-CH₃-5-CF₃Ph CF₃ — COCH₂CH₃ H H141 3-OCH₃-5-CF₃Ph CF₃ — COCH₂CH₃ H H 142 3-CN-5-CF₃Ph CF₃ — COCH₂CH₃ HH 143 2-CH₃-4-CF₃- CF₃ — COCH₂CH(CH₃)OCH₃ H H pyrimidine-6- yl 1442-CF₃-4-CF₃- CF₃ — COCH₂CH₃ H H pyrimidine-6- yl 145 2,6-di-Cl- CF₃ —COCH₂CH₃ H H pyridine-4-yl 146 1-phenyl- CF₃ — COCH₂CH₃ H Hpyrazole-4-yl 147 1-phenyl- CF₃ — COCH₂CH₃ H H pyrazole-3-yl

Although the following indicates several preparation examples accordingto the present invention, the additives and ratios at which theadditives are added are not limited to these examples, but rather can bevaried over a wide range. In addition, the term “parts” in thepreparation examples indicates “parts by weight”.

Preparation Example 1 Wettable Powder

Compound according to the present invention 40 parts Clay 48 partsSodium dioctyl sulfosuccinate  4 parts Sodium lignin sulfonate  8 parts

The above components are uniformly mixed and finely crushed to obtain awettable powder containing 40% active ingredient.

Preparation Example 2 Emulsion

Compound according to the present invention 10 parts Solvesso 200 53parts Cyclohexanone 26 parts Calcium dodecylbenzene sulfonate 1 partPolyoxyethylene alkyl allyl ether 10 parts

The above components are mixed and dissolved to obtain an emulsioncontaining 10% active ingredient.

Preparation Example 3 Powder

Compound according to the present invention 10 parts Clay 90 parts

The above components are uniformly mixed and finely crushed to obtain apowder containing 10% active ingredient.

Preparation Example 4 Granules

Compound according to the present invention 5 parts Clay 73 partsBentonite 20 parts Sodium dioctyl sulfosuccinate 1 part Potassiumphosphate 1 part

The above components are thoroughly crushed and mixed followed by theaddition of water, mixing well, granulating and drying to obtaingranules containing 5% active ingredient.

Preparation Example 5 Suspension

Compound according to the present invention 10 parts Polyoxyethylenealkyl allyl ether 4 parts Sodium polycarboxylate 2 parts Glycerin 10parts Xanthan gum 0.2 parts Water 73.8 parts

The above components are mixed and wet-crushed to a grain size of 3microns or less to obtain a suspension containing 10% active ingredient.

Preparation Example 6 Water-Dispersible Granules

Compound according to the present invention 40 parts Clay 36 partsPotassium chloride 10 parts Sodium alkylbenzene sulfonate 1 part Sodiumlignin sulfonate 8 parts Formaldehyde condensation product of 5 partssodium alkylbenzene sulfonate

The above components are uniformly mixed and finely crushed followed byadding a suitable amount of water and mixing to obtain a clay-likematerial. The clay-like material is granulated and then dried to obtainwater-dispersible granules containing 40% active ingredient.

Among the harmful organism control agents according to the presentinvention obtained in the manner described above, test examples 1 to 3were conducted on the compounds 10 to 12.

Test Example 1 Efficacy Against Aphis gossypii

Cucumber plants planted in a no. 3 pot for which 10 days had elapsedsince germination were inoculated with adult Aphis gossypii. The adultinsects were removed after 1 day, and a chemical liquid diluted withwater to a compound concentration of 500 ppm was sprayed onto thecucumber plants infested with nymphs laid by the adults in accordancewith the emulsion formula indicated in the aforementioned PreparationExample 2. The cucumber plants were placed in a constant temperaturechamber at a temperature of 25° C. and humidity of 65% and insectviability was investigated 5 days later followed by determination ofinsect mortality rate. The test was repeated twice.

As a result, the compounds 10 to 12 demonstrated insect mortality ratesof 100%.

The insect mortality rate of pirimicarb used as a control was 9%.

Test Example 2 Efficacy Against Tetranychus urticae

After inoculating the first true leaves of kidney bean plants planted ina no. 3 pot for which 7 to 10 days had elapsed since germination with 17female adult Tetranychus urticae resistant to organic phosphorousagents, a chemical liquid diluted with water to a compound concentrationof 500 ppm was sprayed onto the kidney bean plants in accordance withthe formula of the wettable powder indicated in the aforementionedPreparation Example 1. The kidney bean plants were placed in a constanttemperature chamber at a temperature of 25° C. and humidity of 65% andinsect mortality rate was investigated 3 days later. The test wasrepeated twice.

As a result, the compounds 10 to 12 demonstrated insect mortality ratesof 100%.

The insect mortality rate of chlordimeform used as a control was 40%.

Test Example 3 Efficacy Against Spodoptera litura

The emulsion indicated in the aforementioned Preparation Example 2 wasdiluted with water to a compound concentration of 500 ppm in accordancewith the formula thereof. After immersing cabbage leaves in the chemicalliquid for 30 seconds and allowing to air dry, the cabbage leaves wereplaced in a Petri dish lined with filter paper and inoculated with five2nd instar Spodoptera litura larvae. A glass cover was placed over thePetri dish, the dish was placed in a constant temperature chamber at atemperature of 25° C. and humidity of 65%, and viability wasinvestigated 5 days later followed by determination of insect mortalityrate. The test was repeated twice.

As a result, the compounds 10 to 12 demonstrated insect mortality ratesof 100%.

INDUSTRIAL APPLICABILITY

According to the present invention, novel nitrogen-containing compoundsor salts thereof, which can be advantageously synthesized industriallyand can function as an active ingredient of a harmful organism controlagent that has reliable effects and can be used safely, as well as aninsecticide, miticide, sanitary insect pest control agent pest controlagent or harmful organism control agent, which contain as an activeingredient thereof at least one type of these compounds, are provided.

1. A nitrogen-containing compound represented by formula (I) or a saltthereof:

(in formula (I), R⁰ represents a nitro group, hydroxyl group, mercaptogroup, a halogen atom, an optionally substituted amino group or anorganic group; Z represents an optionally substituted aryl group, anoptionally substituted heterocyclic group, an optionally substitutedalkyl group, an optionally substituted alkenyl group or an optionallysubstituted alkynyl group; R³ represents a hydrogen atom, an optionallysubstituted aryl group, an optionally substituted heterocyclic group, anoptionally substituted alkyl group, an optionally substituted alkenylgroup, an optionally substituted alkynyl group or an acyl group; Qrepresents a group represented by formula (I′):

(in formula (I′), Y represents a nitro group, hydroxyl group, mercaptogroup, a halogen atom, an optionally substituted amino group or anorganic group; n represents an integer of 0 to 3, a plurality of Y maybe identical to or different from each other when n is 2 or more, andtwo Y may from a 4-membered to 6-membered ring by bonding together whentwo Y are mutually adjacent, D represents a 5-membered to 8-memberedhydrocarbon ring group or heterocyclic group that has or does not have asubstituent other than a substituent X; X represents a group representedby formula (II-1):

(in formula (II-1), R¹ and R² respectively and independently represent ahydrogen atom, nitro group, hydroxyl group, mercapto group, anoptionally substituted amino group, or an organic group. R¹ and R² maybond together to form a 3-membered to 8-membered ring, R¹ or R² may bondto A to form a 5-membered to 8-membered ring), or formula (II-2):

(in formula (II-2), W represents an oxygen atom or sulfur atom, R¹¹represents hydrogen atom, hydroxyl group, mercapto group, an optionallysubstituted amino group, or an organic group), A represents a carbonatom or nitrogen atom, and when A is a carbon atom and does not have asubstituent represented by Y on the carbon atom, hydrogen atom bondthereto or A forms a ring by bonding to R¹ or R², n1 represents aninteger of 0 to 2, and two X are identical to or different from eachother when n1 is 2)).
 2. The nitrogen-containing compound or the saltthereof according to claim 1, wherein, in formula (II-1), R¹ isrepresented by formula (III):

(in formula (III), R¹³⁰ represents a hydrogen atom, hydroxyl group,mercapto group, a halogen atom, an optionally substituted amino group,or an organic group, W represents an oxygen atom or sulfur atom).
 3. Thenitrogen-containing compound or the salt thereof according to claim 1,wherein in formula (I), Q is represented by formula (IV):

(in formula (IV), A, Y, n, X and n1 have the same meaning as defined informula (I′)).
 4. The nitrogen-containing compound or the salt thereofaccording to claim 1, wherein, in formula (I), Z represents anoptionally substituted phenyl group, or an optionally substituted5-membered or 6-membered heterocyclic group including at least oneheteroatom selected from the group consisting of a nitrogen atom, oxygenatom and sulfur atom.
 5. The nitrogen-containing compound or the saltthereof according to claim 1, wherein in formula (I), R⁰ represents a C1to C12 haloalkyl group.
 6. The nitrogen-containing compound or the saltthereof according to claim 1, wherein, in formula (I′), Y represents ahalogen atom, a C1 to C6 alkyl group, a C1 to C6 alkoxy group, a C1 toC6 haloalkyl group or a C1 to C6 haloalkoxy group, or n represents
 0. 7.An insecticide comprising as an active ingredient thereof at least onetype of the nitrogen-containing compound or the salt thereof accordingto any one of claims 1 to
 6. 8. A miticide comprising as an activeingredient thereof at least one type of the nitrogen-containing compoundor the salt thereof according to any one of claims 1 to
 6. 9. A sanitarypest control agent comprising as an active ingredient thereof at leastone type of the nitrogen-containing compound or the salt thereofaccording to any one of claims 1 to
 6. 10. A harmful organism controlagent comprising as an active ingredient thereof at least one type ofthe nitrogen-containing compound or the salt thereof according to anyone of claims 1 to 6.